Allyl chloride → (3-Chloropropyl)(triethyl)silane

Participants

Reaction Steps

In a 25 ml apparatus, there were combined 11.6 g (0.1 mol) of Et3SiH and 0.05 ml of Pt catalyst solution. Heat was applied to 60° C. and addition of a mixture of 7.7 g (0.1 mol) of allyl chloride and 1.4 g (0.01 mol) of Cl3SiH begun. There was a smooth exothermic reaction up to 80° C. by the end of the addition (15 min) with temperature continuing to rise to 129° C. 5 min later. Vacuum distillation yielded 12.12 g (63.0%) of Et3SiCH2CH2CH2Cl, with a Et3SiCH2CH2CH2Cl/Et3SiCl molar ratio of 2.73. This example shows that low levels of Cl3SiH effectively promote both rate and yield of the reaction between Et3SiH and allyl chloride, particularly when the low levels are maintained throughout the reaction by replenishment.

Provenance & Evidence