Sodium hydride → tert-Butyl prop-2-ynyl[3-(tetrahydro-2H-pyran-2-yloxy)propyl]carbamate

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Reaction Steps

A solution of tert-butyl prop-2-ynylcarbamate (1.2 g) in anhydrous N,N-dimethylformamide (5 ml) was treated with 60% sodium hydride (0.245 g) in one portion. After evolution of hydrogen had ceased 2-(3-bromopropoxy)tetrahydro-2H-pyran (1.36 g) was added. The reaction mixture was stirred under nitrogen for 48 hours then diluted with water (50 ml) and extracted into ethyl acetate (3×25 ml). The combined extracts were dried over anhydrous sodium sulphate, filtered and concentrated to afford the sub-titled compound (1.61 g) as a colourless oil.

Provenance & Evidence