Pyridine → HCID 12960803, compound

HRID 1863457Notes

Reaction equation

HRID 1863457 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 argon inlet and mechanical stirrer. Pyridine (230 ml., 2.9 mol) was added and the mixture was stirred for 2 hours. Celite (290 g.) was added and then E-4,4-dimethoxy-2-fluoro-3-methyl-buten-1-ol was added in one portion and stirred for 30 minutes. The mixture was filtered, evaporated at 30° C. to ~5% of its volume and diluted with 500 ml. of ether. This mixture was filtered and evaporated to ~100 ml. at 30° C. The resulting E-4,4-dimethoxy-2-fluoro-3-methyl-buten-1-al was used in the next step without further purification.

Workup

  1. customround bottomed flask fitted with argon inlet and mechanical stirrer
  2. additionCelite (290 g.) was added
  3. stirringstirred for 30 minutes
  4. filtrationThe mixture was filtered
  5. customevaporated at 30° C. to ~5% of its volume
  6. additiondiluted with 500 ml
  7. filtrationThis mixture was filtered
  8. customevaporated to ~100 ml
  9. customat 30° C
  10. customThe resulting E-4,4-dimethoxy-2-fluoro-3-methyl-buten-1-al was used in the next step without further purification

Sources & evidence

ORD record
ord-efbbbb2936af4978a0d13f16ae529e03
Source dataset
uspto-grants-1979_09
Patent number
US04169100

Reaction notes

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