Methyl iodide → 4-(5-Methoxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

HRID 1690726

反応式

HRID 1690726 の反応式
[OH:1][CH2:2][C:3]1[N:7]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[O:10][C:9]2([CH3:20])[CH3:19])[CH:6]=[N:5][CH:4]=1.[H-].[Na+].[CH3:23]I>CN(C=O)C>[CH3:23][O:1][CH2:2][C:3]1[N:7]([CH:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[O:10][C:9]2([CH3:20])[CH3:19])[CH:6]=[N:5][CH:4]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 577811224-(5-Hydroxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

生成物 1

HCID 248026914-(5-Methoxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-(5-hydroxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one (0.125 g, 0.495 mmol) (Example 6d) in DMF (2 mL) is added sodium hydride (0.018 g, 0.495 mmol). The reaction mixture is stirred at room temperature for 5 min and then methyl iodide (0.028 mL, 0.495 mmol) is added. The reaction is stirred for 2.5 h at room temperature. It is then washed with water and extracted with ethyl acetate twice. The organic layer is dried over Na2SO4 and concentrated in vacuo. The residue is purified by silica gel chromatography (dichloromethane-methanol, 19:1) to give 4-(5-methoxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one; MS (ESI) m/z 287.2 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 1.70 (s, 3H), 1.77 (s, 3 H), 3.90 (s, 3 H), 4.39 (s, 2 H), 4.88 (br. s, 1 H), 6.99 (s, 1 H), 7.44-7.53 (m, 1H), 7.56-7.64 (m, 2 H), 7.76 (s, 1 H), 7.86 (d, J=7.6 Hz, 1 H).

後処理

  1. stirringThe reaction is stirred for 2.5 h at room temperature
  2. washIt is then washed with water
  3. extractionextracted with ethyl acetate twice
  4. dry with materialThe organic layer is dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by silica gel chromatography (dichloromethane-methanol, 19:1)

出典と根拠

ORDレコード
ord-42d2962b92d64e009480798e2fa586b5
出典データセット
uspto-grants-2012_04
特許番号
US08153674B2

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