Acetone → 7-fluoro-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one

HRID 490955

반응식

HRID 490955 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[C:4]([OH:11])[CH:3]=1.[CH3:12][C:13]([CH3:15])=O.N1CCCC1>C1C=CC=CC=1>[F:1][C:2]1[CH:3]=[C:4]2[C:5]([C:8](=[O:10])[CH2:9][C:13]([CH3:15])([CH3:12])[O:11]2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 180AcetoneHCID 31268PyrrolidineHCID 27373264'-Fluoro-2'-hydroxyacetophenone

생성물 1

HCID 152053737-fluoro-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one수율 53%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

1-(4-Fluoro-2-hydroxy-phenyl)-ethanone (5.0 g, 32.44 mmol), acetone (11.92 mL, 162.2 mmol) and pyrrolidine (2.7 mL, 32.44 mmol) were dissolved in 20 mL benzene, and the reaction mixture was refluxed for four hours. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and 1 N HCl. The organic layer was dried over MgSO4, and solvent was evaporated under reduced pressure. The resulting residue was chromatographed (15% ethyl acetate in hexanes eluting through silica) and solvent was removed to yield 3.33 g (17.16 mg, 53%) of 7-fluoro-2,2-dimethyl-chroman-4-one as an oil. MS: 195 (M+H)+.

후처리

  1. temperaturethe reaction mixture was refluxed for four hours
  2. custompartitioned between ethyl acetate and 1 N HCl
  3. dry with materialThe organic layer was dried over MgSO4, and solvent
  4. customwas evaporated under reduced pressure
  5. customThe resulting residue was chromatographed (15% ethyl acetate in hexanes eluting through silica) and solvent
  6. customwas removed

출처 및 근거

ORD 기록
ord-4df5a3bcc2434497a2a7b54276b5a6ba
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528250B2

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