Benzyl Alcohol → Benzyloxytrimethylsilane

HRID 500046Notes

Reaction equation

HRID 500046 reaction equation
Cl[Si:2]([CH3:5])([CH3:4])[CH3:3].[CH2:6]([OH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN1C=CN=C1>>[CH3:3][Si:2]([O:13][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([CH3:5])[CH3:4]

Participants

4

Reactant 3

HCID 244Benzyl AlcoholHCID 13901-MethylimidazoleHCID 6397Chlorotrimethylsilane

Product 1

HCID 518982BenzyloxytrimethylsilaneYield 88%

Conditions

Temperature
0 °C

Procedure

5.50 g (51.0 mmol) of chlorotrimethylsilane were added dropwise to a solution of 5.00 g (46.0 mmol) of benzyl alcohol and 4.20 g (51.0 mmol) of 1-methylimidazole while stirring at 0° C. The reaction mixture was stirred for a further 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 7.30 g (theory: 8.29 g) of benzyl trimethylsilyl ether as a colorless oil having a purity of 99% (GC).

Workup

  1. stirringThe reaction mixture was stirred for a further 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-4072f268bd744667b4740dcf296a66a4
Source dataset
uspto-grants-2010_08
Patent number
US07767852B2

Reaction notes

Loading…