Phosphorus oxide (P4O10) → Ethyl (E)-4,4,5,5,5-pentafluoropent-2-enoate

HRID 333953Notes

Reaction equation

HRID 333953 reaction equation
[F:1][C:2]([F:15])([C:11]([F:14])([F:13])[F:12])[CH:3](O)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>>[F:1][C:2]([F:15])([C:11]([F:12])([F:13])[F:14])/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

3

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 21883573Ethyl 4,4,5,5,5-pentafluoro-3-hydroxypentanoate

Product 1

HCID 15260846Ethyl (E)-4,4,5,5,5-pentafluoropent-2-enoate

Conditions

Temperature
140 °C

Procedure

Ethyl 4,4,5,5,5-pentafluoro-3-hydroxy-pentanoate (11.9 g from step C) was placed in a 25 ml round-bottom flask and phosphorpentoxid was added in small portions until the educt was almost completely absorbed. The temperature was raised slowly to 140° C. until a brown syrup was obtained. The flask was connected to a distilling apparatus and the product isolated by distillation at reduced pressure (50 mbar, 50° C.). 5.5 g (25.2 mmol, 50% over 2 steps) were obtained which were used directly in the next step.

Workup

  1. customwas almost completely absorbed
  2. customwas obtained
  3. customthe product isolated by distillation at reduced pressure (50 mbar, 50° C.)
  4. custom5.5 g (25.2 mmol, 50% over 2 steps) were obtained which

Sources & evidence

ORD record
ord-79032a1d84ae4d9f8b79cf1f57bf3fc5
Source dataset
uspto-grants-2014_11
Patent number
US08883791B2

Reaction notes

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