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

HRID 428046ノート

反応式

HRID 428046 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-027241b5648d41bc85678b3724c266bd
出典データセット
uspto-grants-2001_11
特許番号
US06313139B1

反応ノート

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