Ethyl (R)-(+)-4,4,4-trifluoro-3-hydroxybutyrate → (3R)-4,4,4-Trifluoro-1,3-butanediol

A solution of ethyl (R)-(+)-4,4,4trifluoro-3-hydroxybutyrate (3.12 g, 16.8 mmol) in diethyl ether (8 mL) was added to a 0–5° C. suspension of lithium aluminium hydride (1.01 g, 26.6 mmol) in diethyl ether (17 mL) over 25 minutes. Upon complete addition, the mixture was stirred at ambient temperature for 20 h. The mixture was cooled to 0–5° C. and quenched by dropwise addition of 3N HCl (17 mL), followed by stirring at ambient temperature for 3 h. The liquid portion was decanted away and the salts were washed with additional diethyl ether. The combined organic portions were washed (brine), dried, and evaporated to give the product as a cloudy, colourless oil (2.34 g, 96%).

1. additionUpon complete addition
2. temperatureThe mixture was cooled to 0–5° C.
3. customquenched by dropwise addition of 3N HCl (17 mL)
4. stirringby stirring at ambient temperature for 3 h
5. customThe liquid portion was decanted away
6. washthe salts were washed with additional diethyl ether
7. washThe combined organic portions were washed (brine)
8. customdried
9. customevaporated

ORD record

ord-ab45f9cc3b594e6dae6f222e5215ae55

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07119109B2