Methyl iodide → (E)-methyl 4-(dimethoxymethyl)cinnamate

HRID 1955622ノート

反応式

HRID 1955622 の反応式
CO[C:3]([O:15][CH3:16])([OH:14])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[O:13])=[CH:8][CH:7]=1.[C:17](=[O:20])([O-])[O-].[K+].[K+].[CH3:23]I>CN(C=O)C>[CH3:17][O:20][CH:12]([O:13][CH3:23])[C:9]1[CH:8]=[CH:7][C:6](/[CH:5]=[CH:4]/[C:3]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 865896714-Formylcinnamic acid dimethyl acetal

生成物 1

HCID 23247180(E)-methyl 4-(dimethoxymethyl)cinnamate収率 89%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

4-Formylcinnamic acid dimethyl acetal (Cleeland, Jr., et al., U.S. Pat. No. 3,969,373; Jul. 13, 1976) (20.00 g, 90.00 mmol) and anhydrous potassium carbonate (12.44 g, 90.00 mmol) were stirred in anhydrous DMF (189 mL) for 5 minutes. Methyl iodide (12.8 g, 90.0 mmol) was added and the resulting mixture was stirred vigorously with gentle heating (oil bath at 40° C.) for 18 h. Volatiles were evaporated in vacuo and the residue partitioned between hexanes (400 mL) and water (100 mL). The hexanes layer was dried (magnesium sulfate) and evaporated to give (E)-methyl 4-(dimethoxymethyl)cinnamate as a pale yellow oil (18.98 g, 89%);

後処理

  1. customVolatiles were evaporated in vacuo
  2. customthe residue partitioned between hexanes (400 mL) and water (100 mL)
  3. dry with materialThe hexanes layer was dried (magnesium sulfate)
  4. customevaporated

出典と根拠

ORDレコード
ord-c3268e62f5c64c61934d98e90fc16e73
出典データセット
uspto-grants-1998_07
特許番号
US05776940

反応ノート

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