Ethyl 6-(4-cyanobenzyl)-7-hydroxyheptanoate → Ethyl 6-(4-cyanobenzyl)-7-oxoheptanoate

HRID 1927442Notes

Reaction equation

HRID 1927442 reaction equation
[C:1]([C:3]1[CH:21]=[CH:20][C:6]([CH2:7][CH:8]([CH2:18][OH:19])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[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:18]=[O:19])[CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:20][CH:21]=1)#[N:2]

Participants

4

Reactant 2

HCID 22561016Ethyl 6-(4-cyanobenzyl)-7-hydroxyheptanoateHCID 178418287HCID 178418287, compound

Product 1

HCID 22560992Ethyl 6-(4-cyanobenzyl)-7-oxoheptanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4.6 g (15.90 mmol) of ethyl 6-(4-cyanobenzyl)-7-hydroxyheptanoate in 250 ml of dichloromethane is mixed with 4.11 g (19.08 mmol) of pyridinium chlorochromate (PCC) and stirred at room temperature for 12 hours. After conversion is complete, 10 g of silica gel are added, and the solvent is cautiously concentrated to dryness in vacuo. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:1). 4.09 g (14.23 mmol, 89% of theory) of a colorless solid are obtained.

Workup

  1. addition10 g of silica gel are added
  2. concentrationthe solvent is cautiously concentrated to dryness in vacuo
  3. customThe resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 1:1)
  4. custom4.09 g (14.23 mmol, 89% of theory) of a colorless solid are obtained

Sources & evidence

ORD record
ord-de05fed757aa47debf7427e149d59855
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

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