Ethanol → HCID 70817737, compound

HRID 1753097Notes

Reaction equation

HRID 1753097 reaction equation
[OH-:1].[Na+].[CH:3]([N:6]1[C:10]([C:11]([F:14])([F:13])[F:12])=[C:9](CC#N)[CH:8]=[N:7]1)([CH3:5])[CH3:4].[CH3:18][CH2:19][OH:20]>>[CH:3]([N:6]1[C:10]([C:11]([F:14])([F:13])[F:12])=[C:9]([CH2:18][C:19]([OH:1])=[O:20])[CH:8]=[N:7]1)([CH3:5])[CH3:4]

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 70817665HCID 70817665, compound

Product 1

HCID 70817737HCID 70817737, compoundYield 75%

Conditions

Temperature
60 °C

Procedure

Aqueous sodium hydroxide (150 mL of a 1 M solution) was added to [1-isopropyl-5-(trifluoromethyl)-1H-pyrazol-4-yl]acetonitrile (Preparation 106, 6.2 g, 28.6 mmol) in EtOH (150 mL) and the mixture was heated at 60° C. for 16 hours. The mixture was evaporated in vacuo and the residue was dissolved in water (50 mL) then washed with EtOAc (100 mL). The aqueous phase was acidified to pH 5 using 1N HCl and extracted with 10% IPA in DCM (4×100 mL). The combined organic phases were dried over sodium sulphate and evaporated in vacuo to afford the title compound as a white solid in 75% yield, 5.0 g.

Workup

  1. customThe mixture was evaporated in vacuo
  2. dissolutionthe residue was dissolved in water (50 mL)
  3. washthen washed with EtOAc (100 mL)
  4. extractionextracted with 10% IPA in DCM (4×100 mL)
  5. dry with materialThe combined organic phases were dried over sodium sulphate
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-5b8b9bc7730c4e9fb8c47860be77d4c6
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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