Imidazole → 4-(Tert-butyldimethylsilyloxy)-phenyl-acetonitrile

HRID 1295903Notes

Reaction equation

HRID 1295903 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.N1C=CN=C1.[Si:16](Cl)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]>CN(C)C=O.O>[Si:16]([O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1)([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 265484-Hydroxybenzyl cyanideHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 183335824-(Tert-butyldimethylsilyloxy)-phenyl-acetonitrileYield 84.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of (4-hydroxyphenyl)acetonitrile (6.01 g, 45.1 mmol) in N,N-dimethylformamide (60 ml) was treated with imidazole (3.81 g, 58.6 mmol), tert-butyldimethylsilyl chloride (7.49 g, 49.6 mmol) and N,N-dimethylaminopyridine (20 mg) and the resulting solution left to stir at room temperature under a nitrogen atmosphere for 16 hours. The reaction mixture was diluted with water (200 ml) and extracted with ethyl acetate (200 ml×2). The combined organic extracts were washed with sat. aq. sodium chloride (200 ml), dried (sodium sulfate) and the solvent removed in vacuo. Purification by column chromatography on silica gel eluting with ethyl acetate:pentane (0:100 changing to 10:90) gave the title compound as a pale yellow oil (9.44 g).

Workup

  1. waitthe resulting solution left
  2. extractionextracted with ethyl acetate (200 ml×2)
  3. washThe combined organic extracts were washed with sat. aq. sodium chloride (200 ml)
  4. dry with materialdried (sodium sulfate)
  5. customthe solvent removed in vacuo
  6. customPurification by column chromatography on silica gel eluting with ethyl acetate:pentane (0:100 changing to 10:90)

Sources & evidence

ORD record
ord-048ebf73a1b9441a96ffe604446fd0ff
Source dataset
uspto-grants-2007_07
Patent number
US07244766B2

Reaction notes

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