Sodium hydride → Benzyl 3-(2-cyano-3-nitrophenoxy)-2,2-dimethylpropanoate

HRID 1467061노트

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HRID 1467061 반응식
[OH:1][CH2:2][C:3]([CH3:15])([CH3:14])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[H-].[Na+].[N+:18]([C:21]1[CH:28]=[CH:27][CH:26]=[C:25]([N+]([O-])=O)[C:22]=1[C:23]#[N:24])([O-:20])=[O:19]>C1COCC1>[C:23]([C:22]1[C:21]([N+:18]([O-:20])=[O:19])=[CH:28][CH:27]=[CH:26][C:25]=1[O:1][CH2:2][C:3]([CH3:15])([CH3:14])[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])#[N:24]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 520718DinitrobenzonitrileHCID 18922595Benzyl 3-hydroxy-2,2-dimethylpropanoate

생성물 1

HCID 66747122Benzyl 3-(2-cyano-3-nitrophenoxy)-2,2-dimethylpropanoate수율 87.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a solution of benzyl 3-hydroxy-2,2-dimethylpropanoate (Yang, D. et al. J. Am. Chem. Soc. 2002, 124, 9966. 6.68 g, 32.1 mmol) in dry THF (200 mL) was carefully added NaH (60% in mineral oil, 3.5 g, 87.5 mmol) in small portions at 0° C. under nitrogen. The reaction mixture was stirred at 0° C. under nitrogen for 2 hrs. To this solution was added 2,6-dinitrobenzonitrile (6.19 g, 32.1 mmol), and the reaction solution was stirred at 0° C.—RT under nitrogen overnight. The reaction mixture was quenched with brine, and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried over Na2SO4. After evaporation of the solvent, the residue was purified by chromatography on silica gel eluting (Elunet: 20% EtOAc in hexanes) to give the title compound as a brown solid (10.0 g, 87%). MS 355 (MH+).

후처리

  1. customat 0° C.
  2. stirringthe reaction solution was stirred at 0° C.—RT under nitrogen overnight
  3. customThe reaction mixture was quenched with brine
  4. extractionextracted with EtOAc (3×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. customAfter evaporation of the solvent
  8. customthe residue was purified by chromatography on silica gel eluting (Elunet: 20% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-a2d025583c694e6e8a9de952061da223
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09000054B2

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