Methyl 4-trimethylsilylethynylbenzoate → HCID 19068299, compound

Participants

Reaction Steps

3 g (10 mmol) of 3-(1-adamantyl)-4-methoxybenzoyl chloride, 2.3 g (10 mmol) of the above compound (a) and 100 ml of dichloromethane were introduced into a round-bottomed flask. 4.7 g (35 mmol) of AlCl3 were added portionwise, at 0° C., and the mixture was stirred at room temperature for 8 hours. The reaction medium was poured into ice and extracted with dichloromethane. The organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a column of silica, eluted with a mixture of dichloromethane and hexane (80/20). 970 mg (23%) of the expected compound, having a melting point of 156°-8° C., were recovered.

Provenance & Evidence