Sodium hydride → HCID 70029796, 화합물

HRID 413425

반응식

HRID 413425 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 70029796HCID 70029796, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-5008655f7c894778974241fa7dbec834
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06566385B2

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