Triethylamine → Retinal

HRID 346881

反応式

HRID 346881 の反応式
C(N(CC)CC)C.[CH3:8][C:9]1[CH2:14][CH2:13][CH2:12][C:11]([CH3:16])([CH3:15])[C:10]=1/[CH:17]=[CH:18]/[C:19](/[CH3:28])=[CH:20]/[CH:21]=[CH:22]/[C:23](/[CH3:27])=[CH:24]/[CH2:25][OH:26].CCCCCC.C(OCC)C>ClCCl>[CH3:8][C:9]1[CH2:14][CH2:13][CH2:12][C:11]([CH3:15])([CH3:16])[C:10]=1/[CH:17]=[CH:18]/[C:19](/[CH3:28])=[CH:20]/[CH:21]=[CH:22]/[C:23](/[CH3:27])=[CH:24]/[CH:25]=[O:26]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 445354RetinolHCID 21584099Diethylether hexane

生成物 1

HCID 638015Retinal収率 152.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Retinol anhydride (1.00 g, 0.0017 mol) and triethylamine (0.31 g, 0.0021 mol) were added to retinol (0.60 g, 0.0021 mol) dissolved in anhydrous dichloromethane (30 ml) at 0° C. The reaction solution was slowly warmed to room temperature and stirred for 5 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=9/1, v/v) to give 0.91 g (Yield 92%) of the pale yellow title compound. 1H NMR data of this compound were the same as those in Example 1.

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-4e6bd1bee73a46ee881868e8d3871b22
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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