Water → HCID 68714689, compound

HRID 1911570Notes

Reaction equation

HRID 1911570 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:12][CH2:13][C:14]([F:17])([F:16])[F:15])[C:9](O)=[O:10])[CH:5]=[CH:6][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]([CH2:12][CH2:13][C:14]([F:15])([F:16])[F:17])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 68713615HCID 68713615, compound

Product 1

HCID 68714689HCID 68714689, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-(3-chloro-phenyl)-5,5,5-trifluoro-pentanoic acid (1.75 g, 7 mmol) in tetrahydrofuran (40 ml) under an argon atmosphere was added slowly lithium aluminum hydride (0.4 g, 11 mmol) and the mixture was stirred for 17 hours at room temperature. For work-up water (1.5 ml) and 2N sodium hydroxide solution (0.5 ml) were added and the mixture was stirred for 30 min. After filtration the solvent was evaporated and the residue was purified by column chromatography (SiO2, heptane/EtOAc=1:1 to yield a colourless oil, (1.25 g, 75%); MS (EI): 311.0 ((M+OAc)+.).

Workup

  1. stirringthe mixture was stirred for 30 min
  2. filtrationAfter filtration the solvent
  3. customwas evaporated
  4. customthe residue was purified by column chromatography (SiO2, heptane/EtOAc=1:1
  5. customto yield a colourless oil, (1.25 g, 75%)

Sources & evidence

ORD record
ord-6eaf7a50fd8a4d27afc4e4910b71e17b
Source dataset
uspto-grants-2013_12
Patent number
US08604061B2

Reaction notes

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