Hydrochloric Acid → 4-(Adamantan-1-ylmethoxy)-5-(1-((tert-butyldimethylsilyl)oxy)ethyl)-2-fluorobenzoic acid

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Reaction Steps

To a solution of methyl 4-(adamantan-1-ylmethoxy)-5-(1-((tert-butyldimethylsilyl)oxy)-ethyl)-2-fluorobenzoate in tetrahydrofuran (10 mL) was added a solution of lithium hydroxide monohydrate (0.151 g, 3.6 mmol) in water (5 mL) at 0° C. The reaction mixture was allowed to warm to ambient temperature and stirred for 2 days. After adjusting the reaction mixture to pH 5 with 1 N hydrochloric acid, the mixture was extracted with dichloromethane (3×20 mL). The combined organic phase was washed with brine (5 mL), dried over anhydrous sodium sulfate, and filtered. Concentration of the filtrate in vacuo yielded the title compound as a yellowish oil (0.33 g, quant.), which was used without further purification: MS (ES+) m/z 461.4 (M−1).

Provenance & Evidence