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ChemicalBook CAS DataBase List Ethyl (S)-3-hydroxybutyrate
56816-01-4

Ethyl (S)-3-hydroxybutyrate synthesis

8synthesis methods
-

Yield:56816-01-4 73%

Reaction Conditions:

with sulfuric acid

Steps:

4.4. (S)-Ethyl-β-hydroxybutyrate
(S)-3-Hydroxybutyric acid (9.6 g, 92 mmol) was dissolved in 100 mL ethanol with 10 drops of sulfuric acid and stirred in an Erlenmeyerflask. Aliquots (100 μL) were added to 1.0 mL of methanol and analyzed by GC-MS for conversion to product. Upon completion, a small amount of solid sodium bicarbonate was added and the solvent removed by rotary evaporation. The residue was taken up in dichloromethane and washed with water. The water was extracted once with additional dichloromethane and the pooled organic layers dried over magnesium sulfate, filtered, and the solvent removed by rotary evaporation to yield(S)-ethyl-3-hydroxybutyrate as a clear oil (8.9 g, 73%).1H NMR (400 MHz, CDCl3): δ=4.1-4.2 (m, 3H), 2.35-2.48 (m,2H), 1.20 (d, J=6.4 Hz, 3H), 1.25 (t, J=6.9 Hz, 3H)13C NMR: (100 MHz, CDCl3): δ=173.04, 64.30, 60.84, 42.89,22.48, 14.24.

References:

Budin, Noah;Higgins, Erin;DiBernardo, Anthony;Raab, Cassidy;Li, Chun;Ulrich, Scott [Bioorganic Chemistry,2018,vol. 80,p. 560 - 564]

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