tert-Butyl 4-{4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-2-(hydroxymethyl)butyl}benzoate → tert-Butyl 4-{4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-2-formylbutyl}benzoate

HRID 1920592Notes

Reaction equation

HRID 1920592 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[CH2:12]([O:14][C:15](=[O:39])[CH2:16][C:17]1([CH2:20][CH2:21][CH:22]([CH2:37][OH:38])[CH2:23][C:24]2[CH:36]=[CH:35][C:27]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:26][CH:25]=2)[CH2:19][CH2:18]1)[CH3:13]>ClCCl>[CH2:12]([O:14][C:15](=[O:39])[CH2:16][C:17]1([CH2:20][CH2:21][CH:22]([CH:37]=[O:38])[CH2:23][C:24]2[CH:25]=[CH:26][C:27]([C:28]([O:30][C:31]([CH3:32])([CH3:33])[CH3:34])=[O:29])=[CH:35][CH:36]=2)[CH2:19][CH2:18]1)[CH3:13]

Participants

4

Reactant 2

HCID 57965748tert-Butyl 4-{4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-2-(hydroxymethyl)butyl}benzoateHCID 178418287HCID 178418287, compound

Product 1

HCID 57965755tert-Butyl 4-{4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-2-formylbutyl}benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

846 mg (3.93 mmol) of pyridinium chlorochromate (PCC) are added to a solution of 1278 mg (3.27 mmol) of tert-butyl 4-{4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-2-(hydroxymethyl)-butyl}benzoate in 60 ml of dichloromethane, and the mixture is stirred at room temperature for 12 hours. After complete conversion, 5 g of silica gel are added and the solvent is carefully removed to dryness under reduced pressure. The residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 3:1). This gives 1080 mg (85% of theory) of a colorless oil.

Workup

  1. additionAfter complete conversion, 5 g of silica gel are added
  2. customthe solvent is carefully removed to dryness under reduced pressure
  3. customThe residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 3:1)

Sources & evidence

ORD record
ord-3da98c66eb224252b22224b324cb23bb
Source dataset
uspto-grants-2012_05
Patent number
US08168821B2

Reaction notes

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