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

HRID 1177060ノート

反応式

HRID 1177060 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 53682818Methyl 3-(Allyloxy)-5-methoxybenzoate収率 88.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
70 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-9dcd85d480c644738138d17c6ac5dcb8
出典データセット
uspto-grants-2010_11
特許番号
US07842713B2

反応ノート

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