Imidazole → 5-(Tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentan-1-ol

HRID 2065413Notes

Reaction equation

HRID 2065413 reaction equation
[CH3:1][C:2]([CH3:9])([CH2:6][CH2:7][OH:8])[CH2:3][CH2:4][OH:5].N1C=CN=C1.[C:15]([Si:19]([CH3:22])([CH3:21])Cl)([CH3:18])([CH3:17])[CH3:16].O>ClCCl>[C:15]([Si:19]([CH3:22])([CH3:21])[O:5][CH2:4][CH2:3][C:2]([CH3:9])([CH3:1])[CH2:6][CH2:7][OH:8])([CH3:18])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 128107743,3-Dimethylpentane-1,5-diol

Product 1

HCID 107529805-(Tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentan-1-olYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3,3-dimethyl-pentane-1,5-diol (1.5 g, 11 mmol) and imidazole (1.4 g, 20 mmol) in dichloromethane (50 mL) was added tert-butyldimethylchlorosilane (1.7 g, 11 mmol). The reaction mixture was stirred at room temperature for 2 h. Water was added. The organic layer was separated, the aqueous layer was then extracted with dichloromethane. The combined organic layers were washed with brine, dried over MgSO4, concentrated to give 5-(tert-butyl-dimethyl-silanyloxy)-3,3-dimethyl-pentan-1-ol as a colorless oil (2.7 g, 100%).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was then extracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-837db2bf5c5e485f8e9450626f806e14
Source dataset
uspto-grants-2012_10
Patent number
US08288431B2

Reaction notes

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