Ammonia → HCID 13420661, compound

Participants

Reaction Steps

A solution of 1 g (4.8 mmole) of the alcohol product from Example 3 in 15 ml of tetrahydrofuran and 15 ml of t-butyl alcohol was cooled to less than 0°, and 45 ml of distilled liquid ammonia was added. This was followed by the addition over a ten-minute period of 600 mg (86 mmole) of lithium. After three hours, methanol was added to the reaction mixture until the blue color disappeared, and the ammonia was then evaporated under a stream of nitrogen. The residue was dissolved in 5 ml of water, extracted with diethyl ether and acidified with 5% hydrochloric acid. The organic phase was washed with water, dried over magnesium sulfate, filtered, and concentrated to dryness. The residue was chromatographed on silica gel to give 1.26 g of the title compound, contaminated with t-butanol. Structure assignment was confirmed by the proton nmr spectrum.

Provenance & Evidence