Methyl iodide → Methyl 3-(Allyloxy)-5-methoxybenzoate

HRID 1177060노트

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HRID 1177060 반응식
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([OH:10])[CH:7]=[C:6]([O:11][CH2:12][CH:13]=[CH2:14])[CH:5]=1.CI.[C:18]([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([O:10][CH3:18])[CH:7]=[C:6]([O:11][CH2:12][CH:13]=[CH2:14])[CH:5]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 595599953-Allyloxy-5-hydroxybenzoic acid methyl ester

생성물 1

HCID 53682818Methyl 3-(Allyloxy)-5-methoxybenzoate수율 88.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

To a solution of 3-allyloxy-5-hydroxy-benzoic acid methyl ester (1a) (10.25 g, 49.2 mmol) in DMF (20 mL) was added methyl iodide (3.67 mL, 59.1 mmol) and K2CO3 (13.6 g, 98.5 mmol). The reaction mixture was stirred at 70° C. for 2 hr, cooled to room temperature. The mixture was quenched with H2O (150 mL) and extracted with EtOAc (2×150 mL). The organic layers were washed with H2O (2×150 mL), dried over MgSO4 and concentrated to give a pale yellow oil which was purified by flash column chromatography eluting with 10% EtOAc in hexane to give a colorless oil (9.63 g, 88% yield). 1H NMR (400 MHz, CDCl3) δ 7.11-7.24 (m, 2 H) 6.68 (t, J=2.40 Hz, 1 H) 5.91-6.17 (m, 1 H) 5.38-5.51 (m, 1 H) 5.31 (dd, J=10.48, 1.39 Hz, 1 H) 4.52-4.61 (m, 2 H) 3.91 (s, 3 H) 3.83 (s, 3 H); LCMS for C12H14O4 m/z 223.0 (M+H)+.

후처리

  1. temperaturecooled to room temperature
  2. customThe mixture was quenched with H2O (150 mL)
  3. extractionextracted with EtOAc (2×150 mL)
  4. washThe organic layers were washed with H2O (2×150 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto give a pale yellow oil which
  8. customwas purified by flash column chromatography
  9. washeluting with 10% EtOAc in hexane

출처 및 근거

ORD 기록
ord-9dcd85d480c644738138d17c6ac5dcb8
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842713B2

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