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

HRID 428046노트

반응식

HRID 428046 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 10219390chromium (VI) trioxide촉매HCID 6344Dichloromethane용매2회

실험 절차

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),

후처리

  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

출처 및 근거

ORD 기록
ord-027241b5648d41bc85678b3724c266bd
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313139B1

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