Ethyl bromoacetate → HCID 54537755, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 13-7 (1.83 g, 8.4 mmol) in THF (22 mL) at -78° C. was added sodium bis(trimethylsilyl)amide (9.4 mL, 9.4 mmol; 1M/THF) dropwise. After an additional 20 min, ethyl bromoacetate (1.13 mL, 10.3 mmol) was added dropwise. After an additional 20 minutes, the mixture was allowed to warm to 0° C., and 20 mL sat. aqueous NH4Cl was added. The layers were separated, the aqueous layer washed with EtOAc, and the combined organic extracts were dried over K2CO3. Following evaporative removal of the solvent, the residue was chromatographed (silica gel, 40% ethyl acetate/hexanes) to give 13-8 as a colorless oil.

Provenance & Evidence