Idebenone → 10-(4,5-Dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-YL)decanal

HRID 580246

反応式

HRID 580246 の反応式
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C([O-])(=O)C.[Na+].[OH:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]1[C:33](=[O:34])[C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[C:30](=[O:39])[C:29]=1[CH3:40]>ClCCl>[CH:18]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]1[C:33](=[O:34])[C:32]([O:35][CH3:36])=[C:31]([O:37][CH3:38])[C:30](=[O:39])[C:29]=1[CH3:40])=[O:17]

参加物

5

反応物 3

HCID 3686IdebenoneHCID 517045Sodium Acetate2 回HCID 178418287HCID 178418287、化合物2 回

生成物 1

HCID 1351855510-(4,5-Dimethoxy-2-methyl-3,6-dioxocyclohexa-1,4-dien-1-YL)decanal収率 38.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Pyridinium chlorochromate (3.3 g) and sodium acetate (0.5 g) were suspended in dichloromethane (2.5 ml). To the suspension was added a solution of 6-(10-hydroxydecyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (3.38 g) in dichloromethane (20 ml) at room temperature. The mixture was stirred for an hour. Then, additional amount of pyridinium chlorochromate (1 g) and sodium acetate (0.5 g) were added and the mixture was stirred for another 1.5 hours. The reaction mixture was poured into an ice water and the mixture was extracted with ethyl acetate. The extract was treated in a conventional manner and the residue obtained was purified by column chromatography using silica gel. Elution was carried out with dichloroethane-ethyl acetate (9:1) and then with carbon tetrachloride-ethyl acetate (9:1), and the eluate was recrystallized from ethyl acetate-hexane to give 6-(9-formylnonyl)-2,3-dimethoxy-5-methyl-1,4-benzoquinone (1.3 g), melting at 44.5°-46.5° C.

後処理

  1. stirringthe mixture was stirred for another 1.5 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. additionThe extract was treated in a conventional manner
  4. customthe residue obtained
  5. customwas purified by column chromatography
  6. washElution
  7. customwith carbon tetrachloride-ethyl acetate (9:1), and the eluate was recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-554780462233478f88225828dc7cc32e
出典データセット
uspto-grants-1988_06
特許番号
US04751303

関連ノート

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