4-[3-(3,5-Difluoro-4-triisopropylsilanyloxybenzyl)-4-hydroxybutyl]benzonitrile → 4-[3-(3,5-Difluoro-4-triisopropylsilanyloxybenzyl)-4-oxobutyl]benzonitrile

HRID 1921894Notes

Reaction equation

HRID 1921894 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([F:33])[C:21]=1[O:22][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[CH2:5][CH:6]([CH2:17][OH:18])[CH2:7][CH2:8][C:9]1[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[CH:11][CH:10]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([F:33])[C:21]=1[O:22][Si:23]([CH:24]([CH3:26])[CH3:25])([CH:27]([CH3:29])[CH3:28])[CH:30]([CH3:31])[CH3:32])[CH2:5][CH:6]([CH:17]=[O:18])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]#[N:14])=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 579719164-[3-(3,5-Difluoro-4-triisopropylsilanyloxybenzyl)-4-hydroxybutyl]benzonitrileHCID 178418287HCID 178418287, compound

Product 1

HCID 579719344-[3-(3,5-Difluoro-4-triisopropylsilanyloxybenzyl)-4-oxobutyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 750 mg (1.58 mmol) of 4-[3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-4-hydroxybutyl]benzonitrile in 9 ml of dichloromethane is mixed with 409 mg (1.9 mmol) of pyridinium chlorochromate (PCC) and stirred at room temperature for 12 h. After conversion is complete, about 10 g of silica gel are added, and the solvent is removed in vacuo to dryness. The residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→5:1→2:1). 493 mg (64% of theory) of a colorless solid are obtained.

Workup

  1. additionabout 10 g of silica gel are added
  2. customthe solvent is removed in vacuo to dryness
  3. customThe residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→5:1→2:1)
  4. custom493 mg (64% of theory) of a colorless solid are obtained

Sources & evidence

ORD record
ord-5298de75830843bbb016c50aeac9851d
Source dataset
uspto-grants-2012_05
Patent number
US08173704B2

Reaction notes

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