Methyl iodide → HCID 15135018, 화합물

HRID 906093노트

반응식

HRID 906093 반응식
[OH:1][C:2]1[C:3]([CH2:12][CH:13]=[CH2:14])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:15](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C>[CH3:15][O:1][C:2]1[C:3]([CH2:12][CH:13]=[CH2:14])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 22326495HCID 22326495, 화합물

생성물 1

HCID 15135018HCID 15135018, 화합물수율 93%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To methyl 3-hydroxy-2-prop-2-en-1-ylbenzoate (10.3 g, 53.6 mmol, M. A. Eissenstat et al., J. Med. Chem. 1995, 38, 3094-3105) and cesium carbonate (26.2 g, 80.4 mmol) in DMF (100 ml) was added methyl iodide (15.2 g, 102.2 mmol). The reaction mixture was stirred at room temperature for 18 h, then filtered and concentrated. The residue was partitioned between ethyl acetate (250 mL) and water (100 mL). The layers were separated, the organic layer was washed with 5% lithium chloride (2×100 mL) and brine (100 mL), dried over sodium sulfate, and concentrated to provide methyl 3-(methyloxy)-2-prop-2-en-1-ylbenzoate (10.3 g, 93% yield) as a pale yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.41 (m, 1H), 7.24 (m, 1H), 7.02 (m, 1H), 6.97 (m, 1H), 4.97 (m, 2H), 3.88 (s, 3H), 3.85 (s, 3H), 3.73 (m, 2H).

후처리

  1. filtrationfiltered
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate (250 mL) and water (100 mL)
  4. customThe layers were separated
  5. washthe organic layer was washed with 5% lithium chloride (2×100 mL) and brine (100 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0907691a163241fbb6ea880329c83036
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08012956B2

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