반응 #2004696

반응 방정식

(5)-methyl 2-(tert-butyldimethylsilyloxy)-4-hydroxybutanoate

(S)-methyl 2-(tert-butyldimethylsilyloxy)-4-hydroxybutanoate

triethylamine

mesyl chloride

→

(5)-methyl 2-(tert-butyldimethylsilyloxy)-4-mesylbutanoate

용매

dichloromethane

반응 조건

후처리

1. 1
   기타The reaction was quenched with saturated aqueous NH4Cl
2. 2
   추출The aqueous phase was extracted with dicholormethane
3. 3
   세척the combine organic phases were washed with brine
4. 4
   건조The organic layer was dried over anhydrous sodium sulfate
5. 5
   기타the solvent removed in vacuo

실험 절차

To a solution of (5)-methyl 2-(tert-butyldimethylsilyloxy)-4-hydroxybutanoate (91c, 3.9 g, 15.7 mmol) in anhydrous dichloromethane was added triethylamine, DMAP, and mesyl chloride. The reaction was allowed to stir for 1.5 h. The reaction was quenched with saturated aqueous NH4Cl. The aqueous phase was extracted with dicholormethane and the combine organic phases were washed with brine. The organic layer was dried over anhydrous sodium sulfate and the solvent removed in vacuo to yield (5)-methyl 2-(tert-butyldimethylsilyloxy)-4-mesylbutanoate (91d, 4.9 g, 15 mmol) as a yellow oil. [M+H] calc'd for C12H26O6SSi, 327; found, 327.

출처