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

HRID 510598ノート

反応式

HRID 510598 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 152053737-fluoro-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran-4-one収率 70.7%

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1d04325255d647dbac0a31ef4f7c9620
出典データセット
uspto-grants-2015_08
特許番号
US09096567B2

反応ノート

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