Ethyl 8-(4-cyanophenyl)-6-hydroxymethyloctanoate → Ethyl 8-(4-cyanophenyl)-6-formyloctanoate

HRID 1672674Notes

Reaction equation

HRID 1672674 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]([CH2:21][OH:22])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[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]([CH2:9][CH2:10][CH:11]([CH:21]=[O:22])[CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 57831363Ethyl 8-(4-cyanophenyl)-6-hydroxymethyloctanoateHCID 178418287HCID 178418287, compound

Product 1

HCID 57831367Ethyl 8-(4-cyanophenyl)-6-formyloctanoateYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4 g (13.18 mmol) of ethyl 8-(4-cyanophenyl)-6-hydroxymethyloctanoate from Example 85A in 100 ml of dichloromethane is mixed with 3.41 g (15.82 mmol) of pyridinium chlorochromate (PCC) and stirred at room temperature for 12 hours. After conversion is complete, the solvent is concentrated to dryness in vacuo. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→4:1). 2.74 g (9.09 mmol, 69% yield) of a colorless solid are obtained.

Workup

  1. concentrationthe solvent is concentrated to dryness in vacuo
  2. customThe resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→4:1)

Sources & evidence

ORD record
ord-9962aed0cf924ff6b8f0ab5d38424e58
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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