24915-95-5

Ethyl (R)-(-)-3-Hydroxybutyrate is a chiral starting material for the production of numerous biologically active compounds.

clear colorless liquid

Ethyl (R)-(-)-3-hydroxybutyrate is a chiral building block for the preparation of bioactive compounds used in the pharmaceutical industry. It is formed during the hydrolysis of poly-3-hydroxybutyrate.

ChEBI: Ethyl (R)-3-hydroxybutanoate is an ethyl 3-hydroxybutyrate. It is functionally related to a (R)-3-hydroxybutyric acid.

(R)-β-Butryrolactone (20 g, 230 mmol) was dissolved in 500 mLethanol with 1.0 mL H2SO4 and stirred at room temperature. Aliquots(100 μL) were added to 1.0 mL of methanol and analyzed by GC-MS for conversion of the lactone. Upon completion (> 48 h), 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 layer was extracted twice with ethyl acetate. The pooled organic layers were dried with magnesium sulfate, which was then filtered and the solvent removed by rotary evaporation to yield Ethyl (R)-3-hydroxybutyrate as a clear oil (20.2 g, 66%).

[1] AYELET FISHMAN. A two-step enzymatic resolution process for large-scale production of (S)- and (R)-ethyl-3-hydroxybutyrate[J]. Biotechnology and Bioengineering, 2001, 74 3: 256-263. DOI: 10.1002/bit.1115