Potassium Carbonate → 3-chloro-N-(3-ethynyl-1-adamantyl)benzamide

Participants

Reaction Steps

To a stirred mixture of 3-chloro-N-(3-formyl-1-adamantyl)benzamide (350 mg, 1.35 mmol) and K2CO3 (370 mg, 2.7 mmol) in methanol (25 mL) under N2 was added dimethyl (1-diazo-2-oxopropyl)phosphonate (310 mg, 1.62 mmol). After stirring at room temperature for three hours, the clear reaction solution was partitioned between ethyl acetate (20 mL) and 5% NaHCO3 (20 mL) and the aqueous layer was extracted with ethyl acetate (2×20 mL). The combined organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure to yield 210 mg (61%) of the title compound, 3-chloro-N-(3-ethynyl-1-adamantyl)benzamide, as an off-white solid. ESI-MS m/z: 256 (M+H)+.

Provenance & Evidence