2,3-Dimethoxy-p-benzoquinone → Lonapalene

HRID 2107350ノート

反応式

HRID 2107350 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 56237Lonapalene収率 117.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0532a38e91ac40a2b00d5333200d15a6
出典データセット
uspto-grants-1990_06
特許番号
US04933489

反応ノート

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