[OH:1][C:2]([CH3:11])([CH3:10])[CH2:3][CH2:4][CH2:5][C@H:6]([CH3:9])[CH:7]=[O:8].N1C(C)=CC=CC=1C.[Si:20](OS(C(F)(F)F)(=O)=O)([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22]>C(Cl)Cl>[CH3:9][C@@H:6]([CH2:5][CH2:4][CH2:3][C:2]([CH3:10])([O:1][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])[CH3:11])[CH:7]=[O:8]To a solution of aldehyde 9 (93.4 mg, 0.6 mmol) and 2,6-lutidine (170 μL, 1.5 mmol) in anhydrous CH2Cl2 (3.7 mL) was added dropwise Et3SiOTf (161 μL, 0.72 mmol) at 0° C. under argon. The solution was stirred at 10° C. for 3 hours and then at room temperature for 30 minutes. The mixture was quenched with cold water and extracted with CH2Cl2. The solvent was removed under reduced pressure, and the residue was chromatographed on silica Sep-Pak cartridge using hexane/EtOAc (99.7:0.3) as an eluent to give an oily aldehyde 10 (130 mg, 81%).
Loading…
