Trifluoroacetic acid → HCID 178442228, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(2-mercapto-1,3-thiazol-5-yl)pentan-3-ol (515 mg, 2.5 mmol) in 30 ml of CH2Cl2 at 0° C. was added triethylsilane (2.0 ml, 12.5 mmol) and TFA (2.0 ml, 25.9 mmol). The mixture was stirred for 1 h at 0° C. then warmed to room temperature. After 1 h, the reaction mixture was diluted with EtOAc and quenched with a saturated solution of sodium bicarbonate. The layers were separated and the aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous MgSO4 and the solvent evaporated. The crude compound showed a mixture of alkene and desired product. The crude mixture was then resubmitted to the same reaction condition to get complete conversion. The crude was chromatographed on silica gel (hexane:EtOAc; 95:5 to 80:20) to the title compound.

Provenance & Evidence