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

HRID 276800노트

반응식

HRID 276800 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>>[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

4

반응물 3

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

생성물 1

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

반응 조건

온도
40 °C

실험 절차

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-dimethylfornamide (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.

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-9ce82db5ae704ec1b35a9d0810a7d640
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355646B1

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