Potassium Hydroxide → HCID 18687430, compound

Participants

Reaction Steps

A solution of 3-[3 -(tert-butyldimethylsilanyloxymethyl)-4-methoxyphenyl]-3-trifluoromethyl-3H-diazirine (150 mg, 0.41 mmol) in methanol (5 ml) was stirred for 20 min with conc. HCl (2 drops). The solution was poured onto saturated aqueous sodium bicarbonate (10 ml) and extracted with dichloromethane (3×5 ml). The combined organic extracts were dried over sodium sulfate and evaporated under reduced pressure. The residue was taken up in dioxane (3 ml) and aqueous potassium hydroxide (2.5 ml of a 0.2M solution), potassium permanganate (98 mg, 0.62 mmol) was added and the mixture stirred for 4 h. The mixture was filtered through a pad of Celite and washed with water. The filtrate was extracted with ether (2×10 ml). The aqueous phase was brought to pH 1, extracted with ether (2×10 ml) and these extracts were dried over sodium sulfate and evaporated in vacuo to give the title compound (77 mg, 72%) as an off white solid.

Provenance & Evidence