Ethyl bromoacetate → 1-O-benzyl-3-O-t-butyldimethylsilyl-2-O-ethoxycarbonylmethylglycerol

Participants

Reaction Conditions

Reaction Steps

Dried tetrahydrofuran (600 ml) was added to 60% sodium hydride (5.8 g), and the solution cooled to 5° C. A solution (100 ml) of 1-O-benzyl-3-O-t-butyldimethylsilylglycerol (35.9 g) in tetrahydrofuran was added thereto, and the resultant mixture stirred at the same temperature for 2 hours. Then, ethyl bromoacetate (24.3 g) was added dropwise thereto, and the mixture stirred at the same temperature for 2 hours and then room temperature overnight. Upon concentrating the reaction mixture under reduced pressure, water was added to the residue, and the mixture was acidified with 5% hydrochloric acid. After extracting the aqueous layer with ethyl acetate, the extract was washed with saturated brine and dried over anhydrous magnesium sulfate. Upon concentrating thereof under reduced pressure, the residue was purified on a silica gel column (eluent: n-hexane/ethyl acetate=6/1) to obtain the desired product (28.7 g) as oil.

Provenance & Evidence