Water → 1-Butoxy-5-chloro-4,4,5,5-tetrafluoropent-1-en-3-one

HRID 512477Notes

Reaction equation

HRID 512477 reaction equation
[Cl:1][C:2]([F:10])([F:9])[C:3]([F:8])([F:7])[C:4](Cl)=[O:5].N1C=CC=CC=1.[CH:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH2:18].O>C(Cl)(Cl)Cl>[CH2:20]([O:19][CH:17]=[CH:18][C:4](=[O:5])[C:3]([F:8])([F:7])[C:2]([Cl:1])([F:10])[F:9])[CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 8108Butyl vinyl etherHCID 27824993-Chlorotetrafluoropropionyl chloride

Product 1

HCID 866240931-Butoxy-5-chloro-4,4,5,5-tetrafluoropent-1-en-3-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

With stirring and at 0° C., 10.0 g (50.2 mmol) of 3-chlorotetrafluoropropionyl chloride—dissolved in ml of chloroform—were added to a mixture of 3.97 g (50.2 mmol) of pyridine and 5.03 g (50.2 mmol) of butyl vinyl ether in 80 ml of chloroform. After the addition, stirring was continued at room temperature for a further 15 h. 100 ml of water were then added to the mixture, and the organic phase was separated off, dried and concentrated. This gave 10.4 g (78% of theory) of a yellowish oil.

Workup

  1. additionAfter the addition
  2. stirringstirring
  3. customthe organic phase was separated off
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1c995200d66e42449bf44d34def195d6
Source dataset
uspto-grants-2015_08
Patent number
US09102623B2

Reaction notes

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