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

HRID 1955622노트

반응식

HRID 1955622 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 23247180(E)-methyl 4-(dimethoxymethyl)cinnamate수율 89%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
40 °C

실험 절차

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%);

후처리

  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

출처 및 근거

ORD 기록
ord-c3268e62f5c64c61934d98e90fc16e73
출처 데이터셋
uspto-grants-1998_07
특허 번호
US05776940

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