Ammonium Hydroxide → HCID 178516505, compound

HRID 873070Notes

Reaction equation

HRID 873070 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1O[CH:5]=[CH:6][C:7](=[O:9])[CH:8]=1.[OH-].[NH4+:13]>CO>[F:1][C:2]([F:11])([F:10])[C:3]1[CH:8]=[C:7]([OH:9])[CH:6]=[CH:5][N:13]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 108558142-(trifluoromethyl)-4H-pyran-4-one

Product 1

HCID 178516505HCID 178516505, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(trifluoromethyl)-4H-pyran-4-one (350 mg, 2.13 mmol) in MeOH (15 mL) was added ammonium hydroxide (14.8 mL, 107 mmol) at 25° C. The reaction mixture was stirred at 90° C. for 10 h, then concentrated, diluted with water and extracted with ethyl acetate. Combined organic portions were dried over Na2SO4, filtered and concentrated. Purification via Biotage Spla HPFC system (C18, mobile phase: 0.01% NH4HCO3, CH3CN/water, 10˜95%, 9.5 min, 30 mL/min) afforded the title product (280 mg) as a yellow solid.

Workup

  1. concentrationconcentrated
  2. additiondiluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialCombined organic portions were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via Biotage Spla HPFC system (C18, mobile phase: 0.01% NH4HCO3, CH3CN/water, 10˜95%, 9.5 min, 30 mL/min)

Sources & evidence

ORD record
ord-d71d680a9d9f4ca1a7ffe91a9a396b90
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

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