Ethanol → HCID 14360127, compound

Twenty grams of bakers' yeast (Sigma Chemical Company, type II) was suspended in an aqueous solution containing 30 grams of sucrose in a conical flask, and the mixture was placed on an orbital shaker (220 rpm) at 30° C. for 30 minutes to initiate fermentation. Two grams of octyl 2-ethyl acetoacetate was dissolved in 2 ml of 95% ethanol, the resulting solution was added to the fermenting yeast, and shaking was resumed. The reaction was followed by TLC (staining with anisaldehyde) to monitor the consumption of starting material and the production of product alcohol. After approximately 48 hours the reaction was judged complete, and the reaction was terminated by removing from the shaker and adding 20-30 grams of Celite. The resulting suspension was suction filtered through a pad of Celite and the clear yellow filtrate was extracted with ethyl acetate (4×200 ml). The extracts were combined, dried over MgSO4, filtered, and rotary evaporated to leave 1.8 grams of octyl (2R,3S)-2-ethyl-3-hydroxybutyrate as a yellowish oil (>96% enantiomeric excess as judged by chiral chromatography).

1. additionthe resulting solution was added to the fermenting yeast
2. customthe consumption of starting material
3. waitAfter approximately 48 hours the reaction was judged complete
4. customthe reaction was terminated
5. customby removing from the shaker
6. additionadding 20-30 grams of Celite
7. filtrationfiltered through a pad of Celite
8. extractionthe clear yellow filtrate was extracted with ethyl acetate (4×200 ml)
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. customrotary evaporated

ORD record

ord-1f0b284c2f0c4563bf47fb90a1d6bc72

Source dataset

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05834261