1-Methylimidazole → sec-Butoxy(trimethyl)silane

HRID 500044Notes

Reaction equation

HRID 500044 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
0 °C

Procedure

8.06 g (74.2 mmol) of chlorotrimethylsilane were added dropwise to a solution of 5.00 g (67.5 mmol) of 2-butanol and 6.10 g (74.2 mmol) of 1-methylimidazole while stirring at 0° C. The reaction mixture was stirred for another 30 minutes at 0° C. and for 5 minutes at 80° C., resulting in the formation of a liquid two-phase mixture. The upper phase was separated off to give 8.50 g (theory: 9.88 g) of 2-trimethylsilyloxybutane as a colorless, slightly turbid oil having a purity of 96% (GC).

Workup

  1. stirringThe reaction mixture was stirred for another 30 minutes at 0° C. and for 5 minutes at 80° C.
  2. customresulting in the formation of a liquid two-phase mixture
  3. customThe upper phase was separated off

Sources & evidence

ORD record
ord-4fa15f0b08964b9d8195a6947494eb69
Source dataset
uspto-grants-2010_08
Patent number
US07767852B2

Reaction notes

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