Water → HCID 67484566、化合物

HRID 397197

反応式

HRID 397197 の反応式
[CH3:1][O:2][C:3](=[O:18])[C:4]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[C:9]([Cl:17])[CH:8]=1)=[N+]=[N-].[CH:19]1([OH:25])[CH2:24][CH2:23][CH2:22][CH:21]=[CH:20]1.O>ClCCl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH3:1][O:2][C:3](=[O:18])[CH:4]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[C:9]([Cl:17])[CH:8]=1)[O:25][CH:19]1[CH2:24][CH2:23][CH2:22][CH:21]=[CH:20]1

参加物

6

反応物 3

HCID 962WaterHCID 131982-Cyclohexen-1-OLHCID 86584876HCID 86584876、化合物

生成物 1

HCID 67484566HCID 67484566、化合物収率 58%

試薬・触媒・溶媒 2

HCID 423677Acetic acid, rhodium salt (4:2)触媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
25 °C

実験手順

A solution of (3-chloro-4-methanesulfonyl-phenyl)-diazo-acetic acid methyl ester (Example 6; 489 mg, 1.69 mmol) in dichloromethane (10 ML) at 25° C. was treated with 2-cyclohexen-1-ol (0.42 mL, 4.23 mmol) followed by rhodium (II) acetate dimer (15 mg, 0.034 mmol) and the resulting solution was stirred at 25° C. for 1 h. The reaction mixture was diluted with dichloromethane (10 mL), then was poured into water (15 mL) and extracted with dichloromethane (3×10 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The product was purified by chromatography (Biotage Flash 40S column, 75/25 hexanes/ethyl acetate) provided rac-(3-chloro-4-methanesulfonyl-phenyl)-(cyclohex-2-enyloxy)-acetic acid methyl ester (350 mg, 58% yield) as a colorless oil: EI-HRMS m/e calcd for C16H19ClSO5 (M+) 358.0642, found 358.0640.

後処理

  1. extractionextracted with dichloromethane (3×10 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe product was purified by chromatography (Biotage Flash 40S column, 75/25 hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-af9c7fc4d707438fb8b14cbd44dacb9f
出典データセット
uspto-grants-2003_08
特許番号
US06608218B2

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