Methyl 4-[4-(4-cyanophenyl)-2-hydroxymethylbutyl]benzoate → Methyl 4-[4-(4-cyanophenyl)-2-formylbutyl]benzoate

HRID 1672618Notes

Reaction equation

HRID 1672618 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11]([CH2:23][OH:24])[CH2:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=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]([CH2:9][CH2:10][CH:11]([CH:23]=[O:24])[CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=2)=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 57831349Methyl 4-[4-(4-cyanophenyl)-2-hydroxymethylbutyl]benzoateHCID 178418287HCID 178418287, compound

Product 1

HCID 57831348Methyl 4-[4-(4-cyanophenyl)-2-formylbutyl]benzoateYield 73.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5.7 g (17.63 mmol) of methyl 4-[4-(4-cyanophenyl)-2-hydroxymethylbutyl]benzoate from Example 15A in 250 ml of dichloromethane is mixed with 4.56 g (21.15 mmol) of pyridinium chlorochromate (PCC) and stirred at room temperature for 5 hours. After conversion is complete, about 10 g of silica gel are 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). 4.16 g (12.94 mmol, 73% yield) of a colorless solid are obtained.

Workup

  1. additionabout 10 g of silica gel are 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)

Sources & evidence

ORD record
ord-5df38bb251854659b873ef4b6e22db33
Source dataset
uspto-grants-2011_08
Patent number
US07998988B2

Reaction notes

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