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

HRID 512467Notes

Reaction equation

HRID 512467 reaction equation
[CH:1]([F:9])([F:8])[C:2]([F:7])([F:6])[C:3](Cl)=[O:4].N1C=CC=CC=1.[CH:16]([O:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH2:17].O>ClCCl>[CH2:19]([O:18][CH:16]=[CH:17][C:3](=[O:4])[C:2]([F:7])([F:6])[CH:1]([F:9])[F:8])[CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 8108Butyl vinyl etherHCID 27767442,2,3,3-Tetrafluoropropanoyl chloride

Product 1

HCID 911638691-Butoxy-4,4,5,5-tetrafluoropent-1-en-3-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

With stirring and at 0° C., 25.0 g (152 mmol) of 3H-tetrafluoropropionyl chloride—dissolved in 20 ml dichloromethane—were added to a mixture of 14.4 g (182 mmol) of pyridine and 15.2 g (152 mmol) of butyl vinyl ether in 250 ml of dichloromethane. After the addition, stirring was continued at room temperature for another 15 h. 250 ml of water were then added to the mixture, and the organic phase was separated off, dried and concentrated. This gave 12.5 g (36% 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-5e56fafd7a5f45a6890f10a5dfa365be
Source dataset
uspto-grants-2015_08
Patent number
US09102623B2

Reaction notes

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