Methyl 4-[3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-4-hydroxybutyl]benzoate → Methyl 4-[3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-4-oxobutyl]benzoate

HRID 1921886Notes

Reaction equation

HRID 1921886 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([F:35])[C:23]=1[O:24][Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[CH2:5][CH:6]([CH2:19][OH:20])[CH2:7][CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([F:35])[C:23]=1[O:24][Si:25]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:32]([CH3:33])[CH3:34])[CH2:5][CH:6]([CH:19]=[O:20])[CH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 57971911Methyl 4-[3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-4-hydroxybutyl]benzoateHCID 178418287HCID 178418287, compound

Product 1

HCID 57971950Methyl 4-[3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-4-oxobutyl]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2.9 g (5.72 μmmol) of methyl 4-[3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-4-hydroxybutyl]benzoate in 50 ml of dichloromethane is mixed with 1.48 g (6.87 mmol) of pyridinium chlorochromate (PCC) and stirred at room temperature for 12 h. 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). 1.96 g (68% of theory) 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)
  4. custom1.96 g (68% of theory) of a colorless solid are obtained

Sources & evidence

ORD record
ord-81985052a20d43e9985c6ac6d3993181
Source dataset
uspto-grants-2012_05
Patent number
US08173704B2

Reaction notes

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