Tetrabutylammonium Fluoride Trihydrate → (1S,4aR,5R,8aR)-5-((R)-5-Hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-decahydro-naphthalen-1-ol

Participants

Reaction Steps

12.0 g (38.0 mmol) of nBu4NF.3H2O in 40 ml of THF was carefully dried by stirring during 2 h at RT over 15 g of 3 Å molecular sieve. This solution was then added to 1.93 g (4.748 mmol) of (R)-6-[(1R,4aR,5S,8aR)-5-(tert-butyl-dimethyl-silanyloxy)-8a-methyl-decahydro-naphthalen-1-yl]-2-methyl-hept-3-yn-2-ol and the mixture kept for 40 h at 55°. The reaction mixture was then poured onto crushed ice, extracted twice with ether, washed with water and brine, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=8/2) afforded 1.22 g of the title compound as white crystals of mp. 134-135°.

Provenance & Evidence