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

HRID 1690726

반응식

HRID 1690726 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-42d2962b92d64e009480798e2fa586b5
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153674B2

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