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

HRID 333049Notes

Reaction equation

HRID 333049 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.

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

Sources & evidence

ORD record
ord-9b6574d96bf4404f8f2bb3ec10193f51
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

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