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

HRID 370412

반응식

HRID 370412 반응식
[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]

참가 물질

5

반응물 3

HCID 3686IdebenoneHCID 517045Sodium Acetate2회HCID 178418287HCID 178418287, 화합물2회

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-63c2640e310f4330898912a8f0694ec8
출처 데이터셋
uspto-grants-1985_07
특허 번호
US04526719

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