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

HRID 1422151Notes

Reaction equation

HRID 1422151 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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),

Workup

  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

Sources & evidence

ORD record
ord-3ba8289858f94650b8ac2b45adbad5f3
Source dataset
uspto-grants-2000_06
Patent number
US06080773

Reaction notes

Loading…