Imidazole → 2-Methylpentane

HRID 470961Notes

Reaction equation

HRID 470961 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-8521fe02329b445e8dd52695a145fbcb
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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