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

HRID 1021364

반응식

HRID 1021364 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](=O)[CH3:14].N1CCCC1>C1C=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]2[C:5]([C:8](=[O:10])[CH2:9][C:13]([CH3:14])([CH3:12])[O:11]2)=[CH:6][CH:7]=1

참가 물질

6

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 70.7%

시약·촉매·용매 2

HCID 241Benzene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

To 1-(4-fluoro-2-hydroxyphenyl)ethanone (5.75 g, 37.3 mmol) and propan-2-one (12 mL, 37.3 mmol) in benzene (50 mL) was added pyrrolidine (3.11 mL, 37.3 mmol) and the reaction heated at 80° C. for 3 hours. The reaction was diluted with ethyl acetate (50 mL), washed with 1N HCl (50 mL), brine (50 mL), dried over magnesium sulfate and concentrated. The residue was purified by silica gel chromatography, eluting with a gradient of 5% ethyl acetate/hexanes to 50% ethyl acetate, to provide the title compound (5.12 g, 70.7% yield).

후처리

  1. washwashed with 1N HCl (50 mL), brine (50 mL)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with a gradient of 5% ethyl acetate/hexanes to 50% ethyl acetate

출처 및 근거

ORD 기록
ord-59f91cded47049dbb1dbcaa67bbc574a
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716498B2

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