Dichloromethane → Rac-(cyclohex-2-enyloxy)-(3,4-dichloro-phenyl)-acetic acid methyl ester

HRID 1019201

反応式

HRID 1019201 の反応式
[CH3:1][O:2][C:3](=[O:15])[C:4](=[N+]=[N-])[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1.ClCCl.[CH:19]1([OH:25])[CH2:24][CH2:23][CH2:22][CH:21]=[CH:20]1>CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh].O>[CH3:1][O:2][C:3](=[O:15])[CH:4]([O:25][CH:19]1[CH2:24][CH2:23][CH2:22][CH:21]=[CH:20]1)[C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[C:7]([Cl:12])[CH:6]=1

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 131982-Cyclohexen-1-OLHCID 72952160HCID 72952160、化合物

生成物 1

HCID 67484232Rac-(cyclohex-2-enyloxy)-(3,4-dichloro-phenyl)-acetic acid methyl ester収率 78%

試薬・触媒・溶媒 2

HCID 423677Acetic acid, rhodium salt (4:2)触媒HCID 962Water溶媒

反応条件

温度
25 °C

実験手順

In a dry 25 mL round bottom flask under argon was placed diazo-(3,4-dichloro-phenyl)-acetic acid methyl ester (from Example 1, 552 mg, 2.25 mmol), dichloromethane (10 mL) and rac-2-cyclohexen-1-ol (0.45 mL, 4.51 mmol). The solution was stirred at 25° C. and then the rhodium (II) acetate dimer (20 mg, 0.045 mmol) was added. Gas evolution began immediately and the color changed from bright yellow to an aquagreen color. After the solution was stirred at 25° C. for a period of 1 h, it was poured into water and the layers were separated. The aqueous layer was washed with dichloromethane (3×15 mL), then the combined organic layers were dried over sodium sulfate and evaporated under reduced pressure. The residual oil was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 98/2 hexanes/ethyl acetate to afford rac-(cyclohex-2-enyloxy)-(3,4-dichloro-phenyl)-acetic acid methyl ester (552 mg, 78% yield) as a light yellow oil: EI-HRMS m/e calcd for C15H16Cl2O3 (M+) 314.0468, found 314.0476.

後処理

  1. customIn a dry 25 mL round bottom flask under argon was placed
  2. stirringAfter the solution was stirred at 25° C. for a period of 1 h
  3. customthe layers were separated
  4. washThe aqueous layer was washed with dichloromethane (3×15 mL)
  5. dry with materialthe combined organic layers were dried over sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residual oil was purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 98/2 hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-f57dff35fa28409fa741c53ce362aca9
出典データセット
uspto-grants-2002_11
特許番号
US06486184B2

関連ノート

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