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

HRID 1672674ノート

反応式

HRID 1672674 の反応式
[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]

参加物

4

反応物 2

HCID 57831363Ethyl 8-(4-cyanophenyl)-6-hydroxymethyloctanoateHCID 178418287HCID 178418287、化合物

生成物 1

HCID 57831367Ethyl 8-(4-cyanophenyl)-6-formyloctanoate収率 69%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of 4 g (13.18 mmol) of ethyl 8-(4-cyanophenyl)-6-hydroxymethyloctanoate from Example 85A 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% yield) of a colorless solid are obtained.

後処理

  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)

出典と根拠

ORDレコード
ord-9962aed0cf924ff6b8f0ab5d38424e58
出典データセット
uspto-grants-2011_08
特許番号
US07998988B2

反応ノート

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