Methanol → HCID 86650096, compound

HRID 1640092Notes

Reaction equation

HRID 1640092 reaction equation
Br[C:2]([F:15])([F:14])[C:3]([F:13])([F:12])[CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8].CO.[BH4-].[Na+]>O1CCCC1>[F:12][C:3]([F:13])([CH:2]([F:14])[F:15])[CH2:4][CH2:5][CH2:6][C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86650097HCID 86650097, compound

Product 1

HCID 86650096HCID 86650096, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 1 g (3.39 millimoles) of ethyl 6-bromo-5,5,6,6-tetrafluorohexanoate was dissolved in 10 mL of tetrahydrofuran and 1 mL of methanol and then 129 mg (3.39 millimoles) of sodium borohydride was added thereto, followed by stirring at room temperature for 1 hour. A reaction solution was extracted with ethyl acetate after the addition of a sulfuric acid aqueous solution, followed by concentrating a solvent. With this, ethyl 5,5,6,6-tetrafluorohexanoate was obtained at a yield of 50%. There cannot be confirmed production of 6-bromo-5,5,6,6-tetrafluorohexan-1-ol.

Workup

  1. extractionA reaction solution was extracted with ethyl acetate
  2. additionafter the addition of a sulfuric acid aqueous solution
  3. concentrationby concentrating a solvent

Sources & evidence

ORD record
ord-1886981a607e4dd78ccb106bda2f94c1
Source dataset
uspto-grants-2012_02
Patent number
US08110711B2

Reaction notes

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