Hydrochloric Acid → HCID 69507503, compound

Participants

Reaction Steps

Triethylsilyl trifluromethanesulfonate (15 mL) is added dropwise to a −78° C. solution of (4S)-4-hydroxy-5-methyl-6-(2-(2,2,2-trichloroethoxycarbonyloxymethyl)-thiazol-4-yl)-1,5-hexadiene (7.65 g) and 2,6-lutidine (10 mL) in 50 mL of CH2Cl2. After the addition, the reaction mixture is allowed to warm to ambient temperature and is stirred for 5 hours. The reaction mixture is poured into 2 N HCl and extracted with ether. The combined organic layers were washed with 10% aq NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated. Flash chromatography on SiO2 (hexanes/ethyl acetate, 20:1) provides the product as a colorless oil (9.39 g).

Provenance & Evidence