Pyridine → HCID 12960803, compound

HRID 1156430Notes

Reaction equation

HRID 1156430 reaction equation
N1C=CC=CC=1.[CH3:7][O:8][CH:9]([O:16][CH3:17])[CH:10]([CH3:15])/[C:11](/[F:14])=[CH:12]\[OH:13]>[O-2].[O-2].[O-2].[Cr+6].C(Cl)Cl>[CH3:7][O:8][CH:9]([O:16][CH3:17])/[C:10](/[CH3:15])=[C:11](/[F:14])\[CH:12]=[O:13]

Participants

5

Reactant 2

HCID 1049PyridineHCID 86736271HCID 86736271, compound

Product 1

HCID 12960803HCID 12960803, compound

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

Chromium trioxide (145 g., 1.45 mol) was added to 5 l. of methylene chloride in a 12 l. round bottomed flask fitted with an argon inlet and mechanical stirrer. Pyridine (230 ml., 2.9 mol) was added thereto and the resulting mixture was stirred for 2 hours. Celite (290 g.) and then E-4,4-dimethoxy-2-fluoro-3-methyl-buten-1-ol was added in one portion thereof and stirring continued for 30 minutes. The resulting mixture was filtered, evaporated at 30° C. to about 5% of its volume and diluted with 500 ml. of ether. The diluted mixture was filtered and evaporated to about 100 ml. at 30° C. to yield E-4,4-dimethoxy-2-fluoro-3-methyl-buten-1-al.

Workup

  1. customround bottomed flask fitted with an argon inlet and mechanical stirrer
  2. stirringstirring
  3. waitcontinued for 30 minutes
  4. filtrationThe resulting mixture was filtered
  5. customevaporated at 30° C. to about 5% of its volume
  6. additiondiluted with 500 ml
  7. filtrationThe diluted mixture was filtered
  8. customevaporated to about 100 ml

Sources & evidence

ORD record
ord-1181d0a3dd8a46e69ebef3e969c0492c
Source dataset
uspto-grants-1982_06
Patent number
US04335248

Reaction notes

Loading…