Sodium hydride → HCID 70029796、化合物

HRID 413425

反応式

HRID 413425 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[O:15])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH2:18]([O:20][C:21](=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25]CBr)[CH3:19]>CN(C=O)C>[CH2:18]([O:20][C:21](=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][C:9]1([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=[O:15])[CH3:19]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 858682-(3-Methoxyphenyl)cyclohexanoneHCID 117544Ethyl 6-bromohexanoate

生成物 1

HCID 70029796HCID 70029796、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

2-(3-Methoxy-phenyl)-cyclohexanone (0.80 g, 4.05 mmol) was added slowly to a suspension of NaH (60%) (0.185 g, 5.1 mmol) in anhydrous DMF (5 mL) at 0° C. under Ar over 15 min. After an additional 15 min. at 20° C. 6-bromohexanoic acid ethyl ester (1.0 g, 4.5 mmol) was added followed by stirring at 60° C. for 6 hr. The reaction mixture was cooled, quenched with saturated NH4Cl solution, partitioned between EtOAc (150 mL) and H2O (100 mL), the organic layer washed with H2O (2×100 mL), dried (Na2SO4), filtered, and concentrated to dryness to give the title compound after silica gel chromatography eluting with hexane:EtOAc, 50:1 to 10:1.

後処理

  1. temperatureThe reaction mixture was cooled
  2. customquenched with saturated NH4Cl solution
  3. custompartitioned between EtOAc (150 mL) and H2O (100 mL)
  4. washthe organic layer washed with H2O (2×100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

出典と根拠

ORDレコード
ord-5008655f7c894778974241fa7dbec834
出典データセット
uspto-grants-2003_05
特許番号
US06566385B2

関連ノート

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