2,3-Dimethoxy-p-benzoquinone → Lonapalene

HRID 2107352노트

반응식

HRID 2107352 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>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]

참가 물질

4

반응물 2

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

생성물 1

HCID 56237Lonapalene수율 203.1%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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##

후처리

  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

출처 및 근거

ORD 기록
ord-248cfa3ba8a0455b8a56b6ab461caaa2
출처 데이터셋
uspto-grants-1990_06
특허 번호
US04933489

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