Tetrabutylammonium Fluoride → HCID 17893978, compound

Participants

Reaction Steps

To a stirred solution of 1.178 g (3.12 mmole) of [1(R*),3aR* (3aα,4β,7aβ)]-3a,4,5,6,7,7a-hexahydro-1-[1-methyl-5-ethyl-5-hydroxy-3-heptynyl)-7a-methyl-4-[(trimethylsilyl)oxy]-3H-indene in 15 ml anhydrous tetrahydrofuran was added 6 ml (6 mmole) of 1M tetrabutyl ammonium fluoride. The reaction mixture was stirred at room temperature overnight in an argon atmosphere. It was then diluted with 150 ml of water-brine 1:1 and extracted thoroughly with ethyl acetate. The combined extracts were washed with 2×30 ml water, dried over sodium sulfate and evaporated to dryness. The crude product was purified by FLASH chromatography to give 900 mg (94.5%) of the title compound, as a white crystalline solid.

Provenance & Evidence