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

HRID 1422151Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1422151
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

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 10219390chromium (VI) trioxideKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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),

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3ba8289858f94650b8ac2b45adbad5f3
Quelldatensatz
uspto-grants-2000_06
Patentnummer
US06080773

Notizen zur Reaktion

Wird geladen…