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

HRID 1913785Notes

Reaction equation

HRID 1913785 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[C:12]([C:14]1[CH:35]=[CH:34][C:17]([CH2:18][CH:19]([CH2:32][OH:33])[CH2:20][CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=2)=[CH:16][CH:15]=1)#[N:13]>ClCCl>[C:12]([C:14]1[CH:15]=[CH:16][C:17]([CH2:18][CH:19]([CH:32]=[O:33])[CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:30][CH:31]=2)=[CH:34][CH:35]=1)#[N:13]

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

320 mg (1.48 mmol) of pyridinium chlorochromate (PCC) are added to a solution of 400 mg (1.24 mmol) of methyl 4-[3-(4-cyanobenzyl)-4-hydroxybutyl]benzoate from Example 48A in 7 ml of dichloromethane, and the mixture is stirred at room temperature for 5 hours. After conversion is complete, about 1 g of silica gel is 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→4:1). 302 mg (90% purity, 69% of theory) of a colourless solid are obtained.

Workup

  1. additionabout 1 g of silica gel is 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→4:1)
  4. custom302 mg (90% purity, 69% of theory) of a colourless solid are obtained

Sources & evidence

ORD record
ord-9bea25996ee14992805081686e549334
Source dataset
uspto-grants-2013_12
Patent number
US08609727B2

Reaction notes

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