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[ CAS No. 1075-26-9 ] {[proInfo.proName]}

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Chemical Structure| 1075-26-9
Chemical Structure| 1075-26-9
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Product Details of [ 1075-26-9 ]

CAS No. :1075-26-9 MDL No. :MFCD02179595
Formula : C9H9NO Boiling Point : -
Linear Structure Formula :- InChI Key :WRMZOPANDOHWJU-UHFFFAOYSA-N
M.W : 147.17 Pubchem ID :2773459
Synonyms :

Safety of [ 1075-26-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1075-26-9 ]

* 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 [ 1075-26-9 ]

[ 1075-26-9 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 50820-65-0 ]
  • [ 1075-26-9 ]
YieldReaction ConditionsOperation in experiment
95% With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 3h;Under nitrogen; Preparation XLVII 6-((triisopropylsilyloxy)methyl)indole indole-6-carboxylic Acid Methyl Ester [0339] To a solution of indole-6-carboxylic acid (39.5 g, 245 mmol) in methanol (200 mL) and dichloromethane (750 mL) was added 2 M (trimethylsilyl)diazomethane in hexanes (160 mL, 320 mmol) dropwise over 1 hour. The reaction was stirred at room temperature overnight. The following day the reaction was concentrated to a thick brown crude oil that was diluted with ethyl acetate (500 mL) and washed with saturated aqueous sodium bicarbonate (2×200 mL), saturated aqueous sodium chloride (2×200 mL) and dried over sodium sulfate. The mixture was then filtered and the filtrate concentrated under reduced pressure to form a suspension. The suspension was filtered to provide 43 g of the desired compound as an off-white solid. [0340] 6-(hydroxymethyl)indole [0341] To a solution of <strong>[50820-65-0]indole-6-carboxylic acid methyl ester</strong> (20.0 g, 114 mmol) in anhydrous tetrahydrofuran (1.6 L) stirring under nitrogen at room temperature was added carefully lithium aluminum hydride (8.7 g, 230 mmol) while purging with nitrogen. Following this addition, the reaction mixture was stirred at room temperature for 3 hours and was then cooled to 0 C. This mixture was treated sequentially with water (9 mL), 15% sodium hydroxide (9 mL), and additional water (25 mL). The resulting suspension was filtered and the filtrate concentrated under reduced pressure. The residue was subjected to silica gel chromatography, eluting with 30%-60% ethyl acetate in hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 16.0 g (95%) of the desired compound as an off-white solid. [0342] IS-MS, m/e 146.0 (m-1). [0343] Silylation [0344] To a solution of 6-(hydroxymethyl)indole (16.0 g, 110 mmol) in dichloromethane (800 mL) stirring at 0 C. under nitrogen was added triethylamine (22.5 mL, 160 mmol). Next a prepared solution of triisopropylsilyl trifluoromethanesulfonate (30.5 mL, 115 mmol) in dichloromethane (200 mL) was added slowly using an addition funnel. The reaction was stirred at 0 C. for 3 hours. The reaction was then diluted with dichlormethane (200 mL) and washed with water (2×200 mL), saturated aqueous sodium chloride (2×200 mL) and dried over sodium sulfate. The solution was filtered and the filtrate concentrated under reduced pressure. The residue was sujected to silica gel chromatography. Fractions containing product were combined and concentrated under reduced pressure to provide the title compound. [0345] IS-MS, m/e 302 (m-1).
With hydrogenchloride; In tetrahydrofuran; sodium-dried tetrahydrofuran; water; EXAMPLE 9 6-Hydroxymethyl indole Lithium aluminium hydride (3.48 g, 91.70 mmol) was suspended in sodium-dried tetrahydrofuran (150 ml). The suspension was stirred under a nitrogen atmosphere. Methyl-(indol-6-yl)methanoate (8.0 g, 45.7 mmol) was dissolved in dry tetrahydrofuran (50 ml) and added dropwise to the lithium aluminium hydride suspension. The mixture was stirred at ambient temperature for three hours. Water (10 ml) was added dropwise, followed by 2N hydrogen chloride (30 ml). The mixture was extracted with diethyl ether (3*150 ml) to yield a light purple oil.
2.05 g To a suspension of lithium aluminium hydride (0.866 g; 22.82 mmol) in dry THF (30 mL) cooled at 0 C was added a solution of methyl 1 /-/-indole-6-carboxylate (2.000 g; 1 1 .42 mmol) in THF (30 mL) under nitrogen atmosphere. The reaction mixture was stirred at room temperature overnight. The reaction was quenched by careful addition of a 1 N Rochelle salt solution. The reaction mixture was stirred at room temperature for 2 h and was then extracted with dichloromethane. The phases were separated. The organic phase was dried over magnesium sulfate and evaporated under reduced pressure to afford 2.050 g of (1 /-/-indolyl-6-yl)methanol as a yellow oil which was used in the next step without further purification. ESI/APCI(-): 146 (M- H).
  • 2
  • aqueous sodium sulfate [ No CAS ]
  • [ 50820-65-0 ]
  • [ 1075-26-9 ]
YieldReaction ConditionsOperation in experiment
82% With hydrogenchloride; diisobutylaluminium hydride; In methanol; toluene; a. 6-Hydroxymethylindole A stirred solution of <strong>[50820-65-0]methyl indole-6-carboxylate</strong> (50 g) (see Example 1, part b) in dry toluene (1 liter), in a three-necked three-liter flask fitted with a mechanical stirrer, thermometer and dropping funnel, was cooled to -70 under an atmosphere of nitrogen, and treated dropwise with a solution of diisobutylaluminum hydride (381 ml of 1.5M solution in toluene) over 50 min. After 2.5 hr a further portion of diisobutylaluminum hydride (25 ml) was added dropwise, and the mixture stirred for a further 30 min. Methanol (100 ml) and saturated aqueous sodium sulfate (100 ml) were added sequentially, at -78. The cooling bath was removed, the reaction allowed to warm to room temperature, and 6M hydrochloric acid (25 ml) was added dropwise. The mixture was filtered through a pad of diatomaceous earth, the filter cake washed with toluene and water, the organic phase separated and washed with water, dried (MgSO4) and evaporated to give 6-hydroxymethylindole (34.2 g, 82%) as an oil which slowly solidified; partial NMR (250 MHz, CDCl3): 1.73(s, 1H, CH2 OH), 4.78(s, 2H, CH2 OH), 6.55(m, 1H, H3 -indole), 8.20(br s, 1H, NH).
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