Pyridine → Trifluoroethyl 3-methoxytetrafluoropropionate

HRID 35429Notes

Reaction equation

HRID 35429 reaction equation
[CH3:1][O:2][C:3]([F:11])([F:10])[C:4]([F:9])([F:8])[C:5](Cl)=[O:6].[CH2:12]([OH:17])[C:13]([F:16])([F:15])[F:14].N1C=CC=CC=1>C(Cl)Cl>[CH3:1][O:2][C:3]([F:11])([F:10])[C:4]([F:9])([F:8])[C:5]([O:17][CH2:12][C:13]([F:16])([F:15])[F:14])=[O:6]

Participants

5

Reactant 3

HCID 1049Pyridine2×HCID 64092,2,2-TrifluoroethanolHCID 128460263-Methoxy-2,2,3,3-tetrafluoropropionyl chloride

Product 1

HCID 13571089Trifluoroethyl 3-methoxytetrafluoropropionate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroethyl 3-methoxytetrafluoropropionate was prepared by reaction of 97.3 g (0.50 mol) of 3-methoxytetrafluoropropionyl chloride, 55.0 g (0.55 mol) of trifluoroethanol, and 39.5 g (0.50 mol) of pyridine in 100 mL methylene chloride. Reaction was extremely slow until the pyridine was added. After having stirred overnight, the reaction mixture was filtered, solids were rinsed with methylene chloride, and filtrates were distilled to give 119.4 g of ester, bp 44°-49° (20 mm, 2.7 kPa). The cloudy product was treated with 2 g of P2O5 and filtered to afford 109.3 g (93%) of the desired ester, pure by GC. IR (CCl4): 2855, 2975, and 3010 (sat'd CH), 1790 (C=O), and 1300-1100 cm-1 (CF, C--O).

Workup

  1. customReaction
  2. additionwas added
  3. filtrationthe reaction mixture was filtered
  4. washsolids were rinsed with methylene chloride, and filtrates
  5. distillationwere distilled

Sources & evidence

ORD record
ord-8bfce538f6834544aeb05f98a8b3ed34
Source dataset
uspto-grants-1988_08
Patent number
US04766248

Reaction notes

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