반응 #353205

반응 방정식

NaOH

epichlorohydrin

(3α,5β,7α,12α)-3,7,12-trihydroxy-cholan-24-oic acid 1,1-dimethylethyl ester

→

desired product

수율 37.0%

(3α,5β,7α,12α)-3-(2,3-epoxypropyl)oxy-7,12-dihydroxy-cholan-24-oic acid 1,1-dimethylethyl ester

수율 37.0%

용매

CH2Cl2

반응 조건

후처리

1. 1
   기타kept at 0° C.
2. 2
   기타prepared
3. 3
   workup.ADDITIONWhen the addition
4. 4
   workup.WAITwas left
5. 5
   기타to react at room temperature by 24 h
6. 6
   기타The organic phase was separated
7. 7
   세척washed with H2O to neutral,
8. 8
   건조dried over Na2SO4
9. 9
   기타evaporated
10. 10
    기타The residue was purified by flash chromatography

실험 절차

A mixture of 50% NaOH (10 ml), epichlorohydrin (6 ml) and tetrabutylammonium hydrogen sulfate (0.3 g) kept at 0° C. was added drop by drop to a solution of (3α,5β,7α,12α)-3,7,12-trihydroxy-cholan-24-oic acid 1,1-dimethylethyl ester (prepared according to the procedure described by R. P. Bonar-Law et al., J. Chem. Soc. Perkin Trans. I, 1990, 2245) (0.0045 mol) in CH2Cl2 (10 ml). When the addition was completed the mixture was left to react at room temperature by 24 h. The organic phase was separated, washed with H2O to neutral, dried over Na2SO4 and evaporated. The residue was purified by flash chromatography to obtain 0.86 g of desired product (0.0017 mol).

출처