Diethyl Ether → HCID 13407681, compound

Participants

Reaction Conditions

Reaction Steps

2.02 g of magnesium and 30 mL of ethyl ether were charged to a 100 mL three-neck round bottom flask to which 6.3 g of 2-chloropropane was then gradually added to prepare a Grignard solution. 10.7 g of titanium (IV) isopropoxide and 3.7 g of vinyltrimethylsilane were added to another 100 mL three-neck round bottom flask cooled to −78° C., and the above-prepared Grignard solution was gradually added thereto over 30 min. The thus-prepared reaction solution was warmed to −50° C. and vigorously stirred for 2 hours. The reaction solution was maintained at −50° C. while 3.5 g of ethyl acetate was gradually added over 30 min. 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. The reaction solution was warmed to room temperature and 7 mL of saturated brine was added to the solution. The resulting solution was filtered through Celite which was then thoroughly washed once more with 20 mLL of ether. The thus-obtained filtrate was dried over anhydrous magnesium sulfate (MgSO4), and was concentrated by the evaporation of solvent under low vacuum at a low temperature of less than 30° C. The resulting concentrate was distilled (35-50° C./0.1 mmHg) to thereby give 2.2 g of 1-methyl-1-hydroxy-2-(trimethylsilyl)cyclopropane as a mixture of two isomers, i.e. trans and cis isomers in a ratio of 3 to 5:1. Results of 1H-NMR and 13C-NMR for the major isomer (trans isomer) of the mixture are given below.

Provenance & Evidence