Sodium hydride → (+)-6-(2-Benzofuranyl)methoxy-2-[2-(N,N-dimethylamino)ethyl]tetralin

HRID 382989

反応式

HRID 382989 の反応式
[CH3:1][N:2]([CH2:4][CH2:5][CH:6]1[CH2:15][CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([OH:16])[CH:12]=2)[CH2:7]1)[CH3:3].[H-].[Na+].Cl[CH2:20][C:21]1[O:22][C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[CH:25]=1>CN(C=O)C.C1COCC1.O>[O:22]1[C:23]2[CH:29]=[CH:28][CH:27]=[CH:26][C:24]=2[CH:25]=[C:21]1[CH2:20][O:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([CH2:5][CH2:4][N:2]([CH3:3])[CH3:1])[CH2:15][CH2:14]2

参加物

7

反応物 3

HCID 24758Sodium hydrideHCID 1843482-ChloromethylbenzofuranHCID 21939715(+)-2-[2-(N,N-dimethylamino)ethyl]-6-hydroxytetralin

生成物 1

HCID 18361520(+)-6-(2-Benzofuranyl)methoxy-2-[2-(N,N-dimethylamino)ethyl]tetralin収率 4.9%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a solution of (+)-2-[2-(N,N-dimethylamino)ethyl]-6-hydroxytetralin (0.217 g) in DMF (5 ml) was added sodium hydride (60% in oil, 0.052 g) at room temperature. The reaction mixture was stirred at 50° C. for one hr and cooled to 0° C. A solution of 2-chloromethylbenzofuran (0.187 g) in THF (5 ml) was added to the solution. The reaction mixture was stirred at 0° C. for one hr, diluted with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride, dried, and concentrated. The residue was purified by alumina column chromatography (eluent: ethyl acetate:hexane=1:4) and recrystallized from ethyl acetate-hexane to obtain the titled compound (17 mg).

後処理

  1. temperaturecooled to 0° C
  2. stirringThe reaction mixture was stirred at 0° C. for one hr
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated aqueous sodium chloride
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by alumina column chromatography (eluent: ethyl acetate:hexane=1:4)
  8. customrecrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-12fa2b4e779b47d68e7d335955039faf
出典データセット
uspto-grants-2001_10
特許番号
US06310107B1

関連ノート

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