Benzyl Bromide → HCID 66923500, compound

Participants

Reaction Conditions

Reaction Steps

To a −78° C. tetrahydrofuran solution containing methyl indane-1-carboxylate (2.10 g, 11.9 mmol) from Step A, was added a 1M tetrahydrofuran solution of NaHMDS (23.8 mL, 23.8 mmol). The mixture was stirred at −78° C. for 30 minutes. Benzyl bromide (1.49 mL, 12.5 mmol) was added and the reaction was warmed to 0° C. and stirred for 90 minutes. The reaction was quenched with aqueous sodium bicarbonate and then extracted into EtOAc (3×50 mL) and the combined organic washings were dried over MgSO4 and evaporated. The resulting residue was purified by column chromatography (98/2 hexanes/EtOAc) to afford of methyl 1-benzylindane-1-carboxylate (2.5 g, 79%) as a partially pure oil that was taken to the next step.

Provenance & Evidence