ChemicalBook CAS DataBase List 4-PENTYNOIC ACID

4-PENTYNOIC ACID synthesis

11synthesis methods

Product Name:4-PENTYNOIC ACID
CAS Number:6089-09-4
Molecular formula:C5H6O2
Molecular Weight:98.1

5390-04-5
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$13.00/1g

6089-09-4
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$11.00/1g

Yield:6089-09-4 82%

Reaction Conditions:

with Jones reagent in acetone at 0 - 20; for 1 h;

Steps:

5 pent-4-ynoic acid (30d)
23d (lmL, 10.7 mmol) was dissolved in Acetone and cooled to 0°C. Jones reagent was added dropwise to the solution, under vigorous stirring, until the reaction mixture remained orange. The mixture was allowed to reach r.t., and more Jones reagent wasadded to maintain the orange colour. The reaction mixture was stirred at r.t. for lh, then water was added, and was extracted with Et20 several times, washed with Brine and dried over anhydrous Na2504. The solvent was removed at reduced pressure and the resulting oil purified by flash chromatography on silica gel (Hexane/Et20 8:2). Yield 82%, colourless oil. 1HNMR (400 MHz CDC13-d): ? 2.61-2.59 (m, 2H), 2.52-2.48 (m, 2H), 1.98-1.95 (m, 1H) ppm.

References:

AZIENDA OSPEDALIERA UNIVERSITARIA SENESE;MEYERHANS, Andreas;MARTINEZ DE LA SIERRA, Miguel-Angel;BRAI, Annalaura;FAZI, Roberta;TINTORI, Cristina;BOTTA, Maurizio;ARAQUE, José-Esté;MARTINEZ, Javier WO2016/128541, 2016, A1 Location in patent:Page/Page column 53

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