Ethyl Acetate → HCID 13407681, compound

Participants

Reaction Conditions

Reaction Steps

47.3 g (0.17 mole) of titanium (IV) isopropoxide and 19 g (0.17 mole) of dimethylethylvinylsilane were placed in a 500 ml three-neck round bottom flask cooled to −78° C., and 0.34 mole of an isopropylmagnesium chloride Grignard solution was gradually added thereto for 2 hours. The reaction solution thus obtained was warmed to −50° C. and then vigorously stirred for 2 hours. 14.7 g (0.17 mole) of ethyl acetate was gradually added over 30 min, while the reaction solution was maintained at −50° C. The reaction solution was warmed to −20° C., vigorously stirred for 1 hour, warmed to 0° C., and then vigorously stirred for another 1 hour. Finally, the reaction solution was warmed to room temperature and 60 mL of saturated brine was added to the solution. The resulting solution was filtered through Celite which was then thoroughly washed once more with 100 mL of ether. The filtrate thus obtained was dried over anhydrous magnesium sulfate (MgSO4), and was concentrated by the evaporation of solvent under reduced vacuum at a low temperature of 30° C. or less. The resulting concentrate was distilled under vacuum (40-65° C./0.1 mmHg) to obtain 14.6 g (0.092 mole, yield: 54%) of 1-methyl-1-hydroxy-2-(trimethylsilyl)cyclopropane as a mixture of trans and cis isomers in a ratio of about 3:1. Although they may be used directly without any further purification, the trans and cis isomers were separated by silica gel chromatography and their structures were confirmed.

Provenance & Evidence