Imidazole → HCID 57989036, compound

HRID 1689256Notes

Reaction equation

HRID 1689256 reaction equation
[C:1]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[S:9]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][OH:16])=[CH:10]1.N1C=CN=C1>CN(C=O)C.C(OCC)(=O)C>[C:1]([Si:5]([CH3:7])([CH3:6])[O:16][CH2:15][CH2:14][C:11]1[CH:12]=[CH:13][S:9][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 83731Thiophene-3-ethanol

Product 1

HCID 57989036HCID 57989036, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butylchlorodimethylsilane (3.88 g) was added to a stirred solution of 2-(thiophen-3-yl)ethanol (3.00 g) and 1H-imidazole (4.78 g) in DMF (30 mL) cooled in ice bath. After 16 h, the reaction mixture was diluted with ethyl acetate (300 mL), washed with water (3×150 mL) and evaporated in vacuo. Purification was by silica gel chromatography eluting with isohexane and then 1:5 ethyl acetate:isohexane, to collect the subtitled compound as an oil. Yield 5.2 g.

Workup

  1. temperaturecooled in ice bath
  2. washwashed with water (3×150 mL)
  3. customevaporated in vacuo
  4. customPurification
  5. washeluting with isohexane
  6. custom1:5 ethyl acetate:isohexane, to collect the subtitled compound as an oil

Sources & evidence

ORD record
ord-3cf6edb1f819434b9b4390d2124678da
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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