Water → 4,5,5-Trifluoro-4-penten-1-ol

HRID 1710014Notes

Reaction equation

HRID 1710014 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8](=[C:14]([F:16])[F:15])[CH2:9][CH2:10][C:11](O)=[O:12].O>C(OCC)C>[F:7][C:8](=[C:14]([F:16])[F:15])[CH2:9][CH2:10][CH2:11][OH:12]

Participants

5

Reactant 3

HCID 962WaterHCID 27824474,5,5-trifluoropent-4-enoic AcidHCID 21226445Aluminium lithium hydride

Product 1

HCID 27779334,5,5-Trifluoro-4-penten-1-olYield 57.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred suspension of 0.4 gram (0.01 mole) of lithium aluminum hydride in 20 ml of diethyl ether was added dropwise a solution of 1.5 grams (0.01 mole) of 4,5,5-trifluoro-4-pentenoic acid in 30 ml of diethyl ether. Upon completion of addition the reaction mixture was stirred at ambient temperature for one hour, then 20 ml of water was added carefully. The mixture was filtered and the filtrate concentrated under reduced pressure to give 0.8 gram of 4,5,5-trifluoro-4-penten-1-ol as an oil. The nmr and the ir spectra were consistent with the proposed structure.

Workup

  1. additionUpon completion of addition the reaction mixture
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-55f5c6633b8841daaa2ef5f0a3761a9c
Source dataset
uspto-grants-1990_08
Patent number
US04952580

Reaction notes

Loading…