2,3-Dimethoxy-p-benzoquinone → Lonapalene

HRID 2107352ノート

反応式

HRID 2107352 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>C1C=CC=CC=1>[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 203.1%

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A benzene (8 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 30 hours under an inert atmosphere. After this time, the reaction mixture is concentrated and then dissolved in pyridine (8 ml). Acetic anhydride (3.0 g) is added, and the solution is stirred for 12 hours under an inert atmosphere. The contents are diluted ten-fold with water and extracted with ethyl acetate. The organics are then washed with water, brine, and then dried over sodium sulfate. Concentration, followed by flash chromatography (hexane/ethyl acetate 3:1) affords 2.03 g (93%) of a compound of the formula ##STR5##

後処理

  1. concentrationAfter this time, the reaction mixture is concentrated
  2. dissolutiondissolved in pyridine (8 ml)
  3. additionAcetic anhydride (3.0 g) is added
  4. additionThe contents are diluted ten-fold with water
  5. extractionextracted with ethyl acetate
  6. washThe organics are then washed with water, brine
  7. dry with materialdried over sodium sulfate
  8. concentrationConcentration

出典と根拠

ORDレコード
ord-248cfa3ba8a0455b8a56b6ab461caaa2
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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