HCID 86612272, compound → HCID 66917402, compound
Reaction equation
[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH:18]=[O:19])=[C:12]([Br:20])[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][Si:22]([CH2:25][Mg]Cl)([CH3:24])[CH3:23]>C1COCC1>[C:1]1([S:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH:18]([OH:19])[CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=[C:12]([Br:20])[CH:11]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 3-(4-benzenesulfonyl-2-bromo-phenyl)-propionaldehyde (4.77 g, 13.5 mmol) in THF (40 mL) was added trimethylsilylmethylmagnesium chloride (1M in Et2O, 27.3 mL) at −78° C. under Argon atmosphere. The reaction was allowed to reach 0° C. and was stirred for 3 hours, then quenched by addition of buffer pH=2 KHSO4/Na2SO4 (10%) at 0° C. The mixture was extracted 3 times with EtOAc and the combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. The residue was purified via flash chromatography (hexane/EtOAc, 8/2) to afford 4-(4-benzenesulfonyl-2-bromo-phenyl)-1-trimethylsilanyl-butan-2-ol (4.60 g, 77% yield).