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

HRID 1927433Notes

Reaction equation

HRID 1927433 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-formyloctanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4 g (13.18 mmol) of ethyl 8-(4-cyanophenyl)-6-hydroxymethyloctanoate 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% of theory) 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)
  3. custom2.74 g (9.09 mmol, 69% of theory) of a colorless solid are obtained

Sources & evidence

ORD record
ord-4599b487fcb745c58b8d8873a47373c1
Source dataset
uspto-grants-2012_05
Patent number
US08183271B2

Reaction notes

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