Methyl 4-[3-(4-cyanobenzyl)-4-hydroxybutyl]benzoate → Methyl 4-[3-(4-cyanobenzyl)-4-oxobutyl]benzoate

HRID 1927408Notes

Reaction equation

HRID 1927408 reaction equation
[C:1]([C:3]1[CH:24]=[CH:23][C:6]([CH2:7][CH:8]([CH2:21][OH:22])[CH2:9][CH2:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1)#[N:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8]([CH:21]=[O:22])[CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=2)=[CH:23][CH:24]=1)#[N:2]

Participants

4

Reactant 2

HCID 57831369Methyl 4-[3-(4-cyanobenzyl)-4-hydroxybutyl]benzoateHCID 178418287HCID 178418287, compound

Product 1

HCID 57831360Methyl 4-[3-(4-cyanobenzyl)-4-oxobutyl]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 400 mg (1.24 mmol) of methyl 4-[3-(4-cyanobenzyl)-4-hydroxybutyl]benzoate in 7 ml of dichloromethane is mixed with 320 mg (1.48 mmol) of pyridinium chlorochromate (PCC) and stirred at room temperature for 5 hours. After conversion is complete, about 1 g of silica gel is added, and the solvent is removed to dryness in vacuo. The residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→4:1). 302 mg (90% purity, 69% of theory) of a colorless solid are obtained.

Workup

  1. additionabout 1 g of silica gel is added
  2. customthe solvent is removed to dryness in vacuo
  3. customThe residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→4:1)
  4. custom302 mg (90% purity, 69% of theory) of a colorless solid are obtained

Sources & evidence

ORD record
ord-0f8a4a30c0794a729e69929b56199d9e
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

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