1-Methylimidazole → sec-Butoxy(trimethyl)silane

HRID 898069Notes

Reaction equation

HRID 898069 reaction equation
Cl[Si:2]([CH3:5])([CH3:4])[CH3:3].[CH3:6][CH:7]([OH:10])[CH2:8][CH3:9].CN1C=CN=C1>>[CH3:3][Si:2]([CH3:5])([CH3:4])[O:10][CH:7]([CH2:8][CH3:9])[CH3:6]

Participants

4

Reactant 3

HCID 13901-MethylimidazoleHCID 6397ChlorotrimethylsilaneHCID 6568(+-)-2-Butanol

Product 1

HCID 552845sec-Butoxy(trimethyl)silaneYield 86.1%

Conditions

Temperature
80 °C

Procedure

8.06 g (74.2 mmol) of chlorotrimethylsilane were added dropwise while stirring at 0° C. to a solution of 5.00 g (67.5 mmol) of 2-butanol and 6.10 g (74.2 mmol) of 1-methylimidazole. The reaction mixture was stirred at 0° C. for a further 30 min and at 80° C. for 5 min to form a liquid biphasic mixture. Removal of the upper phase gave 8.50 g (theory: 9.88 g) of 2-trimethylsilyloxybutane as a colorless, slightly cloudy oil having a purity of 96% (GC).

Workup

  1. customto form a liquid biphasic mixture
  2. customRemoval of the upper phase

Sources & evidence

ORD record
ord-aea50d2ee3c3495db2e6100340f5ad9f
Source dataset
uspto-grants-2008_04
Patent number
US07351339B2

Reaction notes

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