Tetrahydrofuran → HCID 66931047, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 29 (0.1 g, 0.314 mmol) in anhydrous toluene (5 mL) was cooled to −78° C., under nitrogen, and trifluoromethyltrimethylsilane (62.5 mg, 0.44 mmol) was added. The mixture was stirred for 15 min at −78° C., then a 1M anhydrous solution of tetrabutylammonium fluoride in THF (0.026 ml, 0.026 mmol) was added and the resultant mixture was gradually warmed to room temperature. After stirring for 12 h at room temperature, the reaction mixture was diluted with 4N HCl solution (2 mL) and stirred for an additional 2 h period. The organic layer was separated and the aqueous layer was extracted with diethyl ether (20 mL). The combined organic layer was washed with aqueous saturated NaHCO3 solution (5 mL) and brine, dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (25% diethyl ether-hexane) and the fraction that contains the product 30 and its hydrate form (2:1 ratio by 1H NMR) was concentrated and dried in high vacuum (in the presence of P2O5) to give pure compound 30 (0.0876 g, 76% yield) as a viscous liquid.

Provenance & Evidence