2,3-Dimethoxy-p-benzoquinone → Lonapalene

HRID 2107350노트

반응식

HRID 2107350 반응식
[CH3:1][O:2][C:3]1[C:4]([CH:6]=[CH:7][C:8](=[O:12])[C:9]=1[O:10][CH3:11])=[O:5].[Cl:13][C:14](=[CH2:19])[CH:15]=[CH:16]OC>ClCCl>[Cl:13][C:14]1[CH:19]=[C:6]2[C:7](=[CH:16][CH:15]=1)[C:8]([O:12][C:3](=[O:2])[CH3:9])=[C:9]([O:10][CH3:11])[C:3]([O:2][CH3:1])=[C:4]2[O:5][C:4](=[O:5])[CH3:6]

참가 물질

4

반응물 2

HCID 765652,3-Dimethoxy-p-benzoquinoneHCID 542901063-Chloro-1-methoxybuta-1,3-diene

생성물 1

HCID 56237Lonapalene수율 117.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A dichloromethane (10 ml) solution of 2,3-dimethoxybenzo-1,4-quinone (1.0 g, 5.9 mmol) and 3-chloro-1-methoxy-1,3-butadiene (1.4 g, 12.0 mmol) is stirred for 24 hours at room temperature under an inert atmosphere. After this time, 80 mg of d,1-camphorsulfonic acid is added and the solution is stirred an additional 12 hours. The mixture is then concentrated and subsequently dissolved in pyridine (15 ml) and acetic anhydride (3.0 g). After stirring for five hours under an inert atmosphere, the solution is concentrated to dryness and taken up in dichloromethane. The organics are washed with water, brine, and then dried (sodium sulfate) and concentrated to afford 1.17 g (58%) of pure 6-chloro-1,4-diacetoxy-2,3-dimethoxynaphthalene.

후처리

  1. concentrationThe mixture is then concentrated
  2. dissolutionsubsequently dissolved in pyridine (15 ml)
  3. stirringAfter stirring for five hours under an inert atmosphere
  4. concentrationthe solution is concentrated to dryness
  5. washThe organics are washed with water, brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0532a38e91ac40a2b00d5333200d15a6
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04933489

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