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Chemical Structure| 542-28-9 Chemical Structure| 542-28-9
Chemical Structure| 542-28-9

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CAS No.: 542-28-9

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Tetrahydro-2H-pyran-2-one is an endogenous metabolite.

Synonyms: δ-Valerolactone; 5-Valerolactone; oxan-2-one

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Product Details of Tetrahydro-2H-pyran-2-one

CAS No. :542-28-9
Formula : C5H8O2
M.W : 100.12
SMILES Code : O=C1CCCCO1
Synonyms :
δ-Valerolactone; 5-Valerolactone; oxan-2-one
MDL No. :MFCD00006645
InChI Key :OZJPLYNZGCXSJM-UHFFFAOYSA-N
Pubchem ID :10953

Safety of Tetrahydro-2H-pyran-2-one

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H227-H302-H315-H318
Precautionary Statements:P210-P264-P270-P280-P301+P312+P330-P302+P352-P305+P351+P338+P310-P332+P313-P362+P364-P370+P378-P403+P235-P501
Class:9
UN#:3082
Packing Group:Ⅲ

Application In Synthesis of Tetrahydro-2H-pyran-2-one

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 542-28-9 ]

[ 542-28-9 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 542-28-9 ]
  • [ 29786-93-4 ]
  • [ 917-54-4 ]
  • [ 2768-16-3 ]
  • 2
  • [ 542-28-9 ]
  • [ 67-56-1 ]
  • [ 50995-48-7 ]
YieldReaction ConditionsOperation in experiment
45% 518 g 6-VALEROLACTONE and 5 ml phosphorous tribromide were fed into a 11 three-necked flask. The mixture was heated up to a temperature of 95 °C to 105 °C under stirring and 550 g bromine were added, while the temperature was kept constant between 100 and 120 °C. Subsequently, 5 ml phosphorus tribromide and 236 g bromine were added at a temperature of 110 °C. After the reaction mixture had been allowed to stand for 30 minutes, it was cooled down to a temperature of 0 to 10 °C. Then, 11 methanol and lg p-toluenesulfonic acid were added, while the temperature was kept constant at 25 °C. After 5 hours of refluxing, the excess material was distilled off and the lower organic layer was separated. The organic layer was then washed with 500 ml of 10percent sodium hydroxide and 500 ml water. After separation of the organic layer, the product was isolated by fractional distillation (139 to 142 °C/28 hPa) and 612.7 g of the title compound were obtained (yield 45percent, purity > 96percent by GC).
  • 3
  • [ 542-28-9 ]
  • [ 2338-18-3 ]
  • [ 1148156-44-8 ]
YieldReaction ConditionsOperation in experiment
100% With aluminum (III) chloride; triethylamine; In 1,2-dichloro-ethane; at 20℃; for 1h; STEP D: Preparation of iV-(indan-2-yl)-5-hydroxypentanamideA solution of 2.7 mL (18.75 mmol) Of Et3N in 5mL of 1,2-dichloroethane was added drop by drop under ice cooling to a suspension of 1.85 g (13.75 mmol) AlCl3 in 1OmL of dichloroethane. At room temperature a solution of 2.33g (13,75 mmol) 2-aminoindane HCl(and Et3N for the solvation of the hydrochloride) and 1.16 mL (12.5 mmol) delta- valerolactone in 7.5mL 1,2-dichloroethane was added to the mixture. After one hour of stirring at room temperature the mixture was quenched with ice water and stirred for another30 minutes. The suspension was filtered by Celite. After adding of dichloromethane, separating of the organic layer, washing it with water, drying it with Na2SO4 and evaporating of the solvent, followed.Yield: 100%; ESI-MS: 234 (M+H+, 100).
  • 4
  • [ 542-28-9 ]
  • [ 68176-57-8 ]
  • [ 1379540-72-3 ]
YieldReaction ConditionsOperation in experiment
79% [0553] Step 2: Synthesis of 4-(5-tert-Butyl-lH-benzoimidazol-2-yl)-butan-l-ol[0554] A mixture of 4-tert-butyl -benzene- 1,2-diamine (lg, 6.09mmol) and valerolactone (0.67g, 6.70mmol, l.leq.) in 4N HC1 aq (5ml) was sealed and heated for 2h at 100°C. LCMS analysis shows remaining diamine. Completion was achieved using excess of valerolactone (~1.3ml, 2eq.) heating at 100° for 4h. The reaction was cooled to RT and basified to pH 12 with a saturated solution of Na2C03. EtOAc (100ml) was added and organic separated, washed with saturated solution of Na2C03, water, brine, dried over Na2S04, filtered and concentrated. The residue was purified by flash columnchromatography over silica gel, eluted with DCM - MeOH from 2percent to 5percent gradually to yield 1.19g (79percent) of a beige solid; MS (ESI+) for C15H22N2O m/z 1 [M+H]+, 247.15; HPLC purity 100percent (ret. time, 1.42 min).1H NMR (500 MHz, CHLOROFORM-d) delta ppm 1.38 (9 H, s), 1.65 - 1.75 (2 H, m), 2.00 (2 H, quin, J=7.17 Hz), 2.98 (2 H, t, J=7.09 Hz), 3.72 (2 H, t, J=5.99 Hz), 7.31 (1 H, dd, J=8.51, 1.58 Hz), 7.48 (1 H, d, J=8.20 Hz), 7.56 (1 H, d, J=1.26 Hz).
67% Compound 319(2R,3R,4S,5R)-2-(6-aminopurin-9-yl)-5-[[4-(5-tert-butyl-lH-benzimidazol-2-yl)butyl- isopropyl-amino]methyl]tetrahydrofuran-3,4-diolHStep 1. Preparation of 4-(5-tert-butyl-lH-benzimidazol-2-yl)butan-l-ol A mixture of 4-tert-butylbenzene-l,2-diamine (646 mg, 3.93 mmol) andtetrahydropyran-2-one (1.18 g, 11.80 mmol) in 50 mL of 4 M HC1 was refluxed for 8 h. Then the mixture was neutralized with K2C03 (aq) to pH = 8. The mixture was extracted with DCM (30 mL x4). The organic layers were concentrated and the residue was purified by SGC (DCM : MeOH = 20 : 1) to afford the product(650 mg, yield: 67 percent) as a pale solid. MS (ESI): m/z 247.7 [M+l]+.
49% Compound 323(2R^R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5 ((4-(5-(tert-butyl) H-benzo[d]imidazol-2- yl)butyl)thio)methyI)tetrahydrofuran-3,4-diolStep 1. Preparation of 4-(5-tert-butyl-lH-benzimidazol-2-yl)butan-l-olA solution of 4-tert-butylbenzene-l,2-diamine (6 g, 36.59 mmol) andtetrahydropyran-2-one (6.09 g, 60.98 mmol) in 4 M HC1 (100 mL) was heated to 100° C overnight. The reaction was evaporated, added water (50 mL), adjusted to pH = 8 with aq. NaHC03, extracted with EA (3x100 mL), washed with water (20 mL) and brine (20 mL), dried and concentrated. The residue was purified by SGC to obtain the product (4.4 g, Yield 49percent). 1H NMR (500 MHz, MeOD): 57.50-7.28 (m, 3H), 3.60 (t, J = 6.5 Hz, 2H), 2.91 (t, J = 7.5 Hz, 2H), 1.90 (t, J = 7.0 Hz, 2H), 1.60 (t, J = 7.0 Hz, 2H), 1.37 (s, 9H) ppm; ESI-MS (m/z): 247.2[M+1]+.
  • 5
  • [ 542-28-9 ]
  • [ 4102-60-7 ]
  • 4-[(9Z,12Z)-octadecadienyl]-(13Z,16Z)-tricosadien-1,4-diol [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% 18-Bromo-octadeca-(6z,9z)-diene (0.50 g, 1.52 mmol) was dissolved in diethyl ether (1.5 mL), magnesium shavings (609 mg, 25.1 mmol) were added to the solution, and then one broken piece of iodine was added to the solution. The mixture was left standing for 10 minutes at room temperature, and then stirred with heating at 45 C. on an oil bath, and 18-bromo-octadeca-(6z,9z)-diene (5.0 g, 15.2 mmol) dissolved in diethyl ether (6 mL) was added dropwise to the mixture. The reaction was allowed at 45 C. for 1 hour, and then the reaction mixture was cooled to room temperature. Then, 6-valerolactone (300 muL, 3.23 mmol) was added to the reaction mixture, and the reaction was allowed at room temperature for 1 hour. Then, the reaction mixture was cooled to 4 C., and filtered, and the filtrate was washed with saturated aqueous sodium hydrogencarbonate. Then, anhydrous sodium sulfate was added to the organic layer for dehydration. The organic layer was filtered, and the solvent was evaporated by using a rotating evaporator to obtain a crude product. The crude product was purified by silica gel chromatography {elution solvent, hexane:ethyl acetate (continuous gradient)} to obtain 4-[(9z, 12z)-octadecadienyl]-(13z, 16z)-tricosadien-1,4-diol (1.64 g, 2.73 mmol) as colorless oil. Yield from 6-valerolactone was 85%. Proton nuclear magnetic resonance (1H NMR, 500 MHz) data of 4-[(9z,12z)-octadecadienyl]-(13z,16z)-tricosadien-1,4-diol delta=0.88 (t, 6H), 1.25-1.1.46 (m, 46H), 2.02-2.06 (m, 8H), 2.77 (t, 4H), 3.66 (t, 2H), 5.30-5.40 (m, 8H)
 

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