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

HRID 333074Notes

Reaction equation

HRID 333074 reaction equation
[F:1][C:2]([F:14])([CH:11]([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:14])([CH:11]([F:12])[F:13])/[CH:3]=[CH:4]/[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

3

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 86691164Ethyl 4,4,5,5-tetrafluoro-3-hydroxy-pentanoate

Product 1

HCID 86691166Ethyl (E)-4,4,5,5-tetrafluoropent-2-enoateYield 76.2%

Conditions

Temperature
80 °C

Procedure

Ethyl 4,4,5,5-tetrafluoro-3-hydroxy-pentanoate (22.9 g, 0.105 mol) was mixed with phosphorus pentoxide (7.5 g, 0.053 mol) and the resulting mixture was stirred at 80° C. for two hours. The product was isolated by vacuum distillation (53 mbar, 92° C.) to yield 15.9 g of a liquid (0.08 mol, 76%) that was used directly in the next step.

Workup

  1. customThe product was isolated by vacuum distillation (53 mbar, 92° C.)

Sources & evidence

ORD record
ord-fec0c505526647c2b1290e1440795208
Source dataset
uspto-grants-2014_11
Patent number
US08877934B2

Reaction notes

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