Chlorotrimethylsilane → [(1-Ethoxy-3-methylbut-1-en-1-yl)oxy](trimethyl)silane

HRID 1758969Notes

Reaction equation

C(NC(C)C)(C)C.C([Li])CCC.[C:13]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:14][CH:15]([CH3:17])[CH3:16].Cl[Si:23]([CH3:26])([CH3:25])[CH3:24]>CCCCCC.O1CCCC1>[CH3:24][Si:23]([CH3:26])([CH3:25])[O:18][C:13]([O:19][CH2:20][CH3:21])=[CH:14][CH:15]([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 0 °C

Procedure

A 1 liter flask was equipped with a mechanical stirrer, a reflux condenser, an addition funnel, nitrogen inlet, and thermometer. The glassware was dried carefully and charged with 225 ml of tetrahydrofuran, 30.36 g (0.300 mol) of diisopropylamine, and cooled to 0° C. Over a 30 minute period, 190 ml (0.300 mol) of 1.6 M n-butyl lithium in hexane was added. The reaction mixture was stirred at 0° C. for 15 min., then cooled to -76° C. and 39.06 g (0.300 mol) of ethyl isovalerate added dropwise over ~15 min. When addition was complete, the reaction mixture was stirred for 15 min. at -76° C., then 82 ml (0.88 mol) of chlorotrimethylsilane added dropwise. When addition was complete, the Dry Ice-acetone bath was removed and the reaction mixture stirred for 11/2 hrs. while coming up to room temperature.

Workup

customA 1 liter flask was equipped with a mechanical stirrer, a reflux condenser, an addition funnel, nitrogen inlet
customThe glassware was dried carefully
temperaturecooled to -76° C.
additionWhen addition
stirringthe reaction mixture was stirred for 15 min. at -76° C.
additionWhen addition
customthe Dry Ice-acetone bath was removed
stirringthe reaction mixture stirred for 11/2 hrs
customcoming up to room temperature

Sources & evidence

ORD record: ord-f60135f959a24ed6b3c71a8b2e5eb7be
Source dataset: uspto-grants-1982_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04338326

Reaction notes

Loading…