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Grignard reagent | Time | Product | Yield |
PrMgCl | 20 min | PhCHClCH2OH | 72% |
MeMgBr | 20 min | PhCHBrCH2OH | 83% |
EtMgBr | 20 min | PhCHBrCH2OH | 75% |
MeMgI | 20 min | PhCHICH2OH/PhCH(OH)CH2I | 90% |
MeMgBr | 6 h | PhCH2CH(OH)CH3 | 80% |
EtMgBr | 6 h | PhCH2CH(OH)Et | 65% |
PhMgBr | 6 h | PhCH2CH(OH)Ph | 84% |
MeMgI | 24 h | PhCH(OH)CH2I | 60% |
To a vigorously stirring solution of styrene oxide (2.4 g) and titanium(IV)isopropoxide (5.7 g) in 100 ml of absolute ether, Grignard reagent (20 ml of 1N solution in ether) was added at room temperature during 15-20 min. The reaction mixture was stirred for time showed in the table and decomposed with 5% sulfuric acid. Two phases was obtained. The organic phase was separated, washed with brine and dried over MgSO4. The solvent was evaporated, and the residue purified by column chromatography (silicagel L100/250, Et2O-hexane 1:3).