Triethylamine → (S)-methyl 2-(tert-butyldimethylsilyloxy)-4-mesylbutanoate

Participants

Reaction Steps

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.

Provenance & Evidence