Tetrabutylammonium Fluoride Trihydrate → HCID 86756379, compound

Participants

Reaction Steps

1.40 g of tetrabutylammoniumfluoride trihydrate (4.45 mmol) in 6 ml of tetrahydrofuran was carefully dried by stirring during 2 h at room temperature over 1.78 g of 3 Å molecular sieve. This solution was then added to the above prepared 270 mg of (1R,3R)-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-5-((2E,9E)-12,12,12-trifluoro-7,7-dimethyl-11-trifluoromethyl-11-trimethylsilanyloxy-dodeca-2,9-dienylidene)-cyclohexane (0.371 mmol) and kept for 1.5 h at 40°. The reaction mixture was then poured onto crushed ice/NH4Cl, extracted twice with ether, washed with water, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/ethylacetate=25/75) yielded 165 mg of the title compound as colourless oil. Typically, this product is contaminated with small amounts of 2Z-isomer which can be removed by HPLC.

Provenance & Evidence