Chlorotrimethylsilane → 4-(2-Methylpropyl)-beta,beta-bis(trimethylsiloxy)styrene

Temperature

0 °C

Butyllithium in hexane (175 ml of 1.6 M solution, 0.28 mol) was added to a solution of 30 g (0.3 mol) of diisopropylamine in 200 ml of tetrahydrofuran at 25° C. The reaction mixture was cooled to 0° C. and a solution of 26.0 g (0.135 mol) of 4-(2-methylpropyl)benzeneacetic acid in 200 ml of tetrahydrofuran was added dropwise near 0° C. The mixture was stirred for 1 hour at 0° C. and then 70 ml (0.55 mol) of trimethylchlorosilane were added. The reaction mixture was warmed to room temperature and stirred for 2 hours. The solid that formed was filtered off; the filtrate was concentrated under reduced pressure and then mixed with 100 ml of diethyl ether. The resultant mixture was filtered and the filtrate was concentrated. Distillation of the residue gave 31.92 g (70% yield) of 4-(2-methylpropyl)-β,β-bis(trimethylsiloxy)styrene as a colorless liquid: bp 128° -130° C. (0.4 mm); ir (liquid) 6.07μ (C=C). Anal. Calcd. for C18H32O2Si2 : C, 64.22; H, 9.58; Found: C, 64.34; H, 9.95.

1. temperatureThe reaction mixture was warmed to room temperature
2. stirringstirred for 2 hours
3. customThe solid that formed
4. filtrationwas filtered off
5. concentrationthe filtrate was concentrated under reduced pressure
6. additionmixed with 100 ml of diethyl ether
7. filtrationThe resultant mixture was filtered
8. concentrationthe filtrate was concentrated
9. distillationDistillation of the residue

ORD record

ord-69cfc69d56b04669868c4963961092e6

Source dataset

uspto-grants-1980_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04215044