Dimethyl Sulfoxide → 1-(2-Fluoro-3-pyridinyl)-1-propanone

HRID 1426681ノート

反応式

HRID 1426681 の反応式
[F:1][C:2]1[C:7]([CH:8]([OH:11])[CH2:9][CH3:10])=[CH:6][CH:5]=[CH:4][N:3]=1.CS(C)=O.C(N(CC)CC)C>O>[F:1][C:2]1[C:7]([C:8](=[O:11])[CH2:9][CH3:10])=[CH:6][CH:5]=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 595867223-Pyridinemethanol, alpha-ethyl-2-fluoro-

生成物 1

HCID 598268711-(2-Fluoro-3-pyridinyl)-1-propanone収率 87.3%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To a mixture of 1-(2-fluoropyridin-3-yl)propan-1-ol (12.3 g), dimethyl sulfoxide (130 mL) and triethylamine (65 mL) was added a sulfur trioxide-pyridine complex (25.6 g), and the mixture was stirred at room temperature for 14 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1) to give the title compound as a brown oil (yield 10.6 g, 87%).

後処理

  1. additionwas added a sulfur trioxide-pyridine complex (25.6 g)
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-6f0881e7436f4b4a9cad9d77878de15f
出典データセット
uspto-grants-2015_01
特許番号
US08933105B2

反応ノート

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