Dicyclohexylcarbodiimide → Retinal

HRID 346880

反応式

HRID 346880 の反応式
[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:22])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:21])=[CH:17]/[C:18](O)=[O:19].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C.CC1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/CO>ClCCl.CCCCCC.C(OCC)C>[CH3:1][C:2]1[CH2:7][CH2:6][CH2:5][C:4]([CH3:8])([CH3:9])[C:3]=1/[CH:10]=[CH:11]/[C:12](/[CH3:22])=[CH:13]/[CH:14]=[CH:15]/[C:16](/[CH3:21])=[CH:17]/[CH:18]=[O:19]

参加物

7

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 444795Retinoic AcidHCID 445354Retinol

生成物 1

HCID 638015Retinal収率 129.7%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21584099Diethylether hexane溶媒

実験手順

Retinoic acid (1.26 g, 0.0042 mol, Basf Co.), dicyclohexylcarbodiimide (DCC) (0.87 g, 0.0042 mol) and catalytic amount of dimethylaminopyridine (DMAP) were added to retinol (1.00 g, 0.0035 mol) dissolved in anhydrous dichloromethane (50 ml) at 0° C. The reaction solution was slowly warmed to room temperature and stirred for 12 hours under nitrogen atmosphere and under the condition for light and moisture to be intercepted. The reaction solution was filtered and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (silica gel 60 for cc part, Merk Co., mesh size 270–400, hexane/diethylether=19/1, v/v) to give 1.55 g (Yield 78%) of the pale yellow title compound.

後処理

  1. filtrationThe reaction solution was filtered
  2. customthe solvent was removed by distillation under reduced pressure
  3. customThe residue was purified by column chromatography (silica gel 60 for cc part, Merk Co

出典と根拠

ORDレコード
ord-9eb3a1f1fd5e4d55865230379739028c
出典データセット
uspto-grants-2007_02
特許番号
US07173062B2

関連ノート

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