Ammonium Chloride → HCID 12136225, compound

Participants

Reaction Conditions

Reaction Steps

18-Crown-6 (349 mg, 1.32 mmol, 2 eq) is added to a solution of bis(2,2,2-trifluoroethyl) (methoxycarbonylmethyl)phosphonate (355 mg, 1.78 mmol, 2.7 eq) in toluene (7 mL) at 23° C. and stirred for 5 min. The mixture is cooled to −20° C. KHMDS (1.78 mmol, 2.7 eq, 0.5 M in toluene) is added dropwise and stirred for 30 min. The mixture is warmed to 0° C. and stirred for 30 min. Then the mixture is cooled to −20° C., a solution of crude (2R,3R,4S,5Z,8S,9R, 10R, 11 S,12S)-3,9-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-11-hydroxy-2,4,6,8,10,12-hexamethyl-13-(phenylmethoxy)-5-tridecenal in toluene (3 mL) is added to the mixture and stirred for 5 min. The mixture is warmed to 0° C. and stirred for 4 h. Saturated NH4Cl (15 mL) is added, and the resultant mixture is washed with brine, dried and concentrated. The crude product is chromatographed (10% EtOAc in hexane) to give 266 mg (two-step: 52%) of the desired compound as a colorless oil.

Provenance & Evidence