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

HRID 891236ノート

反応式

HRID 891236 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)C=O>[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) (20.00 g) and anhydrous potassium carbonate (12.44 g) were stirred in anhydrous N,N-dimethylformamide (189 ml) for 5 minutes. Methyl iodide (12.8 g) 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%), 1H-NMR (DMSO-d6) consistent with structure.

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-ebaa1c820d2649afa9929bc3f4a06ab6
出典データセット
uspto-grants-2006_02
特許番号
US07002012B2

反応ノート

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