Imidazole → 2-Methylpentane

HRID 1689192Notes

Reaction equation

HRID 1689192 reaction equation
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH2:14][CH2:15][OH:16].N1C=CN=C1>CN(C=O)C>[CH3:10][CH2:11][CH2:5][CH:4]([CH3:7])[CH3:6].[C:4]([Si:1]([CH3:3])([CH3:2])[O:16][CH2:15][CH2:14][C:10]1[S:9][CH:13]=[CH:12][CH:11]=1)([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 794002-Thiopheneethanol

Product 2

HCID 78922-MethylpentaneHCID 22503634Tert-butyldimethyl(2-(thiophen-2-YL)ethoxy)silane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyldimethylsilyl chloride (12.66 g) was added portionwise to 2-(2-thienyl)ethanol (9.0 g) and imidazole (5.7 g) in DMF (35 mL). The resulting solution was stirred for 18 h. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, dried over sodium sulphate and the solvents evaporated in vacuo. Purification was by silica gel chromatography, eluting with 99:1 to 96:4 ethyl acetate:isohexane to give the subtitled compound as a clear oil. Yield 16 g.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with water
  3. dry with materialdried over sodium sulphate
  4. customthe solvents evaporated in vacuo
  5. customPurification
  6. washeluting with 99:1 to 96:4 ethyl acetate

Sources & evidence

ORD record
ord-ee61a448d02c4046a7aaf1213a1de6d5
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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