Chlorotrimethylsilane → Trimethylsilyl-3-benzofurancarboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (4 mL) in 20 mL THF at -60° C. was added 2.5 M of n-BuLi in hexane (17 mL), and the solution was stirred at between -20 and -60° C. for 1 h. To this, a solution of 3-benzofurancarboxylic acid (2.6 g) in 30 mL THF was added at <-70° C. After 1 h, TMSCl (7 mL) was added at <-70° C., and stirring was continued for an additional 1 h. The solution was allowed to warm to 0° C., quenched with 2 N HCl and extracted with methylene chloride. The organic solution was washed with brine, dried and concentrated to give 3.6 g of 2-(trimethylsilyl-3-benzofurancarboxylic acid.

Provenance & Evidence