Hydrochloric Acid → 1-(2-Fluoropyridin-4-yl)-2-(3-trifluoromethylphenyl)ethane-1,2-dione-1-oxime

HRID 862208ノート

反応式

HRID 862208 の反応式
[F:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1.C([O:25][N:26]=O)(C)(C)C.Cl>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([C:8](=[N:26][OH:25])[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:19])[F:20])[CH:12]=2)=[O:10])[CH:5]=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 119771402-(2-Fluoropyridin-4-yl)-1-[3-(trifluoromethyl)phenyl]ethanone

生成物 1

HCID 1363810621-(2-Fluoropyridin-4-yl)-2-(3-trifluoromethylphenyl)ethane-1,2-dione-1-oxime

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a mixture of 2-(2-fluoropyridin-4-yl)-1-(3-trifluoromethylphenyl)ethanone (10.80 g, 0.038 mole) in ethanol (200 mL), at -10° C., under argon, was added tert-butylnitrite (5.0 mL, 0.042 mol) followed by hydrogen chloride (12.2 mL, 2.5M in ethanol, 0.031 mole) dropwise while maintaining the temperature below -5° C. Upon completion of addition, the reaction was allowed to warm to room temperature for 2 hours. The reaction was concentrated in vacuo, diluted with water (100 mL), basified with saturated sodium bicarbonate (200ml). This mixture was then extracted with ethyl acetate (1×600 mL, 2×300 mL). The organic layers were combined, washed with water (300 mL), washed with brine (300 mL), dried over anhydrous sodium sulfate, filtered and concentrated to an oil (11.4 g).

後処理

  1. temperaturewhile maintaining the temperature below -5° C
  2. additionUpon completion of addition
  3. concentrationThe reaction was concentrated in vacuo
  4. additiondiluted with water (100 mL)
  5. extractionThis mixture was then extracted with ethyl acetate (1×600 mL, 2×300 mL)
  6. washwashed with water (300 mL)
  7. washwashed with brine (300 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated to an oil (11.4 g)

出典と根拠

ORDレコード
ord-6abde5afbf754b80b3a5c907489def6a
出典データセット
uspto-grants-1998_02
特許番号
US05717100

反応ノート

読み込み中…