Methyl 4-[3-(4-cyanobenzyl)-4-hydroxybutyl]benzoate → Methyl 4-[3-(4-cyanobenzyl)-4-oxobutyl]benzoate
反応式
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[C:12]([C:14]1[CH:35]=[CH:34][C:17]([CH2:18][CH:19]([CH2:32][OH:33])[CH2:20][CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][CH:23]=2)=[CH:16][CH:15]=1)#[N:13]>ClCCl>[C:12]([C:14]1[CH:15]=[CH:16][C:17]([CH2:18][CH:19]([CH:32]=[O:33])[CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:30][CH:31]=2)=[CH:34][CH:35]=1)#[N:13]参加物
4
実験手順
320 mg (1.48 mmol) of pyridinium chlorochromate (PCC) are added to a solution of 400 mg (1.24 mmol) of methyl 4-[3-(4-cyanobenzyl)-4-hydroxybutyl]benzoate from Example 48A in 7 ml of dichloromethane, and the mixture is stirred at room temperature for 5 hours. After conversion is complete, about 1 g of silica gel is added, and the solvent is removed in vacuo to dryness. The residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 10:1→4:1). 302 mg (90% purity, 69% of theory) of a colourless solid are obtained.