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

HRID 512480Notes

Reaction equation

HRID 512480 reaction equation
[Cl:1][C:2]([F:10])([C:6]([F:9])([F:8])[F:7])[C:3](Cl)=[O:4].N1C=CC=CC=1.[CH:17]([O:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH2:18]>ClCCl>[CH2:20]([O:19][CH:17]=[CH:18][C:3](=[O:4])[C:2]([Cl:1])([F:10])[C:6]([F:9])([F:8])[F:7])[CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 8108Butyl vinyl etherHCID 27824982-Chloro-2,3,3,3-tetrafluoropropanoyl chloride

Product 1

HCID 866240961-Butoxy-4-chloro-4,5,5,5-tetrafluoropent-1-en-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

With stirring and at 0° C., 9.59 g (48.2 mmol) of 2-chlorotetrafluoropropionyl chloride were added dropwise to a mixture of 4.19 g (50.0 mmol) of pyridine and 4.83 g (48.2 mmol) of butyl vinyl ether in 75 ml of dichloromethane. After the addition, stirring was continued at room temperature for another 15 h. The mixture was then washed with 1N hydrochloric acid and 2×100 ml of water, and the organic phase was separated off, dried and concentrated. This gave 6.33 g (50% of theory) of a brown oil.

Workup

  1. additionAfter the addition
  2. stirringstirring
  3. washThe mixture was then washed with 1N hydrochloric acid and 2×100 ml of water
  4. customthe organic phase was separated off
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-4ad6f0766f9e4ce5bc41e5dca8b88e96
Source dataset
uspto-grants-2015_08
Patent number
US09102623B2

Reaction notes

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