Silica → (2-Fluoropyridin-3-yl)-2-(diethoxymethyl)-phenylmethanone

HRID 1422151ノート

反応式

HRID 1422151 の反応式
O=[Si]=O.[F:4][C:5]1[C:10]([CH:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]([O:23][CH2:24][CH3:25])[O:20][CH2:21][CH3:22])[OH:12])=[CH:9][CH:8]=[CH:7][N:6]=1>C(Cl)Cl.[O-2].[O-2].[O-2].[Cr+6]>[F:4][C:5]1[C:10]([C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]([O:20][CH2:21][CH3:22])[O:23][CH2:24][CH3:25])=[O:12])=[CH:9][CH:8]=[CH:7][N:6]=1

参加物

5

反応物 2

HCID 24261SilicaHCID 18357530(2-Fluoropyridin-3-yl)-2-(diethoxymethyl)-phenylmethanol

生成物 1

HCID 18357614(2-Fluoropyridin-3-yl)-2-(diethoxymethyl)-phenylmethanone

試薬・触媒・溶媒 2

HCID 10219390chromium (VI) trioxide触媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a stirred suspension of 11.8 g of dicalite in 100 ml of dry methylene chloride was added 7.38 g of chromium trioxide. The suspension was stirred for 30 min then a solution of (2-fluoropyridin-3-yl)-2-(diethoxymethyl)-phenylmethanol in 100 ml of methylene chloride was added. The supension was stirred overnight. The suspension was filtered through dicalite and washed with methylene chloride. The filtrate was washed with 100 ml portions of 1 M sodium hydroxide solution, water and brine and evaporated and azeotroped with toluene. Flash chromatography eluting with 30 to 50% ethyl acetate in heptane afforded (2-fluoropyridin-3-yl)-2-(diethoxymethyl)-phenylmethanone as a gum; 1H-NMR (200 MHz, CDCl3) d 5.60 (CHOEt),

後処理

  1. stirringThe supension was stirred overnight
  2. filtrationThe suspension was filtered through dicalite
  3. washwashed with methylene chloride
  4. washThe filtrate was washed with 100 ml portions of 1 M sodium hydroxide solution, water and brine
  5. customevaporated
  6. customazeotroped with toluene
  7. washFlash chromatography eluting with 30 to 50% ethyl acetate in heptane

出典と根拠

ORDレコード
ord-3ba8289858f94650b8ac2b45adbad5f3
出典データセット
uspto-grants-2000_06
特許番号
US06080773

反応ノート

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