Pyridine → Trifluoroethyl 3-methoxytetrafluoropropionate

HRID 482822Notes

Reaction equation

HRID 482822 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-0b5c246ecb1442b1a3041dc937604888
Source dataset
uspto-grants-1986_03
Patent number
US04576752

Reaction notes

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