Methyl iodide → (3,5-Dimethoxyphenyl)-(2,3,4-trimethoxyphenyl)methanone

HRID 2378180ノート

反応式

HRID 2378180 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[C:14]=2[OH:23])=[O:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.IC.[C:26]([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH3:22])[C:14]=2[O:23][CH3:26])=[O:12])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 69205198(3,5-Dimethoxyphenyl)-(2-hydroxy-3,4-dimethoxyphenyl)methanone

生成物 1

HCID 69203226(3,5-Dimethoxyphenyl)-(2,3,4-trimethoxyphenyl)methanone収率 90%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
35 °C

実験手順

To a mixture of (3,5-dimethoxyphenyl)-(2-hydroxy-3,4-dimethoxyphenyl)methanone (1.59 g, 5.00 mmol) in DMF (25 ml) was added iodomethane (0.62 ml, 10.00 mmol), and powdered Na2CO3 (1.06 g, 10.00 mmol) at rt. The suspension was stirred at ˜35° C. overnight. DMF was evaporated in vacuo and to the residue was added CH2Cl2 (100 ml) and washed with H2O (3×80 ml). The white salt was filtered and the solution was washed with 5 N KOH (4×80 ml), H2O (1×80 ml), dried over MgSO4 and concentrated to a brown oil, which was purified via flash column chromatography (20% EtOAc in hexane) to give (3,5-dimethoxy-phenyl)-(2,3,4-trimethoxy-phenyl)methanone as a clear oil (1.49 g, 90%): 1HNMR (CDCl3) δ 7.12 (d, J=8 Hz, 1H, Ar), 6.94 (d, J=2 Hz, 2H, Ar), 6.71 (d, J=8 Hz, 1H, Ar), 6.65 (t, J=2 Hz, 1H, Ar), 3.93 (s, 3H, OCH3), 3.89 (s, 3H, OCH3), 3.81 (s, 6H, 2OCH3), 3.79 (s, 3H, OCH3); 13C NMR (CDCl3) δ 195.2, 160.7, 156.3, 152.9, 142.2, 140.5, 126.6, 125.1, 107.7, 106.8, 105.4, 62.0, 61.1, 56.3, 55.7; Anal. Calcd. For C18H20O6: C, 65.05; H, 6.07. Found: C, 64.93; H, 6.09. The product was carried over to the next step.

後処理

  1. customDMF was evaporated in vacuo and to the residue
  2. additionwas added CH2Cl2 (100 ml)
  3. washwashed with H2O (3×80 ml)
  4. filtrationThe white salt was filtered
  5. washthe solution was washed with 5 N KOH (4×80 ml), H2O (1×80 ml)
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to a brown oil, which
  8. customwas purified via flash column chromatography (20% EtOAc in hexane)

出典と根拠

ORDレコード
ord-1b875c849a0142f6b3e5fb0af243e7c9
出典データセット
uspto-grants-2008_12
特許番号
US07470723B2

反応ノート

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