Water → methyl 7-(2-methyl-1H-tetrazol-5-yl)-2,3-dihydro-1-benzoxepine-4-carboxylate

HRID 1388046ノート

反応式

HRID 1388046 の反応式
[NH:1]1[C:5]([C:6]2[CH:7]=[CH:8][C:9]3[O:15][CH2:14][CH2:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][C:10]=3[CH:20]=2)=[N:4][N:3]=[N:2]1.[H-].[Na+].[CH3:23]I.O>CN(C=O)C>[CH3:23][N:3]1[NH:2][N:1]=[C:5]([C:6]2[CH:7]=[CH:8][C:9]3[O:15][CH2:14][CH2:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][C:10]=3[CH:20]=2)[NH:4]1

参加物

6

反応物 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178496911HCID 178496911、化合物

生成物 1

HCID 18472406methyl 7-(2-methyl-1H-tetrazol-5-yl)-2,3-dihydro-1-benzoxepine-4-carboxylate収率 79%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In DMF (6 ml) was dissolved methyl 7-(1H-tetrazol-5-yl)-2.3-dihydro-1-benzoxepine-4-carboxylate (400 mg, 1. 47 mmol), and to the mixture was added at 0° C. sodium hydride (60%, 90 mg, 2.3 mmol). The mixture was stirred at the same temperature for 15 minutes, and to the mixture was added at 0° C. methyl iodide (0.28 ml, 4.4 mmol). While the temperature of the mixture was warmed from 0° C. to room temperature, the mixture was stirred for 3 hours. To the mixture was added at 0° C. water (30 ml), and the mixture was extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified with column chromatography (silica gel 40 g, ethyl acetate/hexane=1/8→1/2), and the first eluted desired fraction was concentrated under reduced pressure to give methyl 7-(2-methyl-1H-tetrazol-5-yl)-2,3-dihydro-1-benzoxepine-4-carboxylate (334 mg, 1.17 mmol, 79%). The second eluted desired fraction was concentrated under reduced pressure to give methyl 7-(1-methyl-1H-tetrazol-5-yl)-2,3-dihydro-1-benzoxepine-4-carboxylate (76 mg, 0.27 mmol, 18%).

後処理

  1. temperatureWhile the temperature of the mixture was warmed from 0° C. to room temperature
  2. stirringthe mixture was stirred for 3 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with column chromatography (silica gel 40 g, ethyl acetate/hexane=1/8→1/2)
  7. washthe first eluted desired fraction
  8. concentrationwas concentrated under reduced pressure

出典と根拠

ORDレコード
ord-3ca5de8243934f5384436aeccc506433
出典データセット
uspto-grants-2001_07
特許番号
US06268354B1

反応ノート

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