Water → HCID 178519318, compound

HRID 915380Notes

Reaction equation

HRID 915380 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[NH:8][N:7]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[F:20][C:17]([F:18])([F:19])[C:14]1[CH:13]=[CH:12][C:11]([C:9]2[NH:8][N:7]=[C:6]([CH2:4][OH:3])[CH:10]=2)=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178468625HCID 178468625, compound

Product 1

HCID 178519318HCID 178519318, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 5-(4-trifluoromethyl-phenyl)-1H-pyrazole-3-carboxylic acid ethyl ester (160 mg, 0.56 mmol; PCT Int. Appl. (2003), WO 2004000785 A2) in tetrahydrofuran (2.5 ml) was added to a suspension of lithium aluminium hydride (43 mg, 1.13 mmol) in tetrahydrofuran (2.5 ml) under an argon atmosphere at ambient temperature within 5 min. The mixture was heated to reflux for 12 h, cooled to 0° C. and treated cautiously with water (2 ml) and 10% aqueous NaOH (0.5 ml). The reaction mixture was filtered over celite, ice water/ethyl acetate 1/1 was added and the layers were separated. The aqueous layer was extracted one more time with ethyl acetate, the combined organic layers were washed with ice water/brine 1/1 and dried over sodium sulfate. Removal of the solvent under reduced pressure gave 81 mg (0.33 mmol, 59%) of the title compound as white solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 12 h
  3. filtrationThe reaction mixture was filtered over celite, ice water/ethyl acetate 1/1
  4. additionwas added
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted one more time with ethyl acetate
  7. washthe combined organic layers were washed with ice water/brine 1/1
  8. dry with materialdried over sodium sulfate
  9. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-83b952c0f1c848c29104faab78d5e152
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Reaction notes

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