반응 #58772

반응 방정식

tetrahydrofuran

compound ( 17 )

2-oxo-butyric acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

isopropenylmagnesium bromide

→

title compound

(2S)-2-ethyl-2-hydroxy-3-methyl-but-3-enoic acid (1R,2S,5R)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester

반응 조건

후처리

1. 1
   workup.ADDITIONwere added dropwise at −78° C
2. 2
   기타the reaction mixture was quenched by addition of 110 mL saturated aqueous ammonium chloride solution
3. 3
   추출was extracted twice with 110 mL ethyl acetate
4. 4
   세척The combined organic phases were washed with 110 mL brine
5. 5
   건조dried over 15 g sodium sulfate
6. 6
   여과were filtered
7. 7
   세척The filter cake was washed with 30 mL ethyl acetate
8. 8
   기타The organic phase was evaporated to dryness in a rotary evaporator (40° C., 8 mbar)

실험 절차

To a solution of 4.200 g of compound (17) as obtained from example 11 (13.27 mmol) in 168 mL tetrahydrofuran were added dropwise at −78° C. 39.8 mL isopropenylmagnesium bromide (19.91 mmol, 1.5 eq). After additional 50 min, the reaction mixture was quenched by addition of 110 mL saturated aqueous ammonium chloride solution, and was extracted twice with 110 mL ethyl acetate. The combined organic phases were washed with 110 mL brine, dried over 15 g sodium sulfate and were filtered. The filter cake was washed with 30 mL ethyl acetate. The organic phase was evaporated to dryness in a rotary evaporator (40° C., 8 mbar) yielding the title compound (4.790 g, 101% by weight, dr=93:7)as a yellow oil.

출처