Sodium Hydroxide → 1342905-27-4

HRID 1755277Notes

Reaction equation

HRID 1755277 reaction equation
C([O:3][C:4]([C:6]1[CH:10]=[CH:9][N:8]([CH:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[N:7]=1)=[O:5])C.[OH-].[Na+]>C1COCC1.CO.CCOC(C)=O>[O:14]1[CH2:15][CH2:16][CH:11]([N:8]2[CH:9]=[CH:10][C:6]([C:4]([OH:5])=[O:3])=[N:7]2)[CH2:12][CH2:13]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 90187025HCID 90187025, compound

Product 1

HCID 644495421342905-27-4Yield 80.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(Tetrahydro-pyran-4-yl)-1H-pyrazole-3-carboxylic acid ethyl ester (1.14 g, 5.09 mmol) was dissolved in a mixture of THF (5.0 mL) and MeOH (5.0 mL). To this was added NaOH (20% aqueous, 5.0 mL). The reaction mixture was stirred overnight and was then diluted with EtOAc and washed with 1 M NaHSO4. The aqueous layer was extracted with EtOAc and the combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to give the product as a white solid (802 mg, 80%).

Workup

  1. washwashed with 1 M NaHSO4
  2. extractionThe aqueous layer was extracted with EtOAc
  3. dry with materialthe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c6a040d20ce645a8a5c49a241856cb21
Source dataset
uspto-grants-2015_10
Patent number
US09169261B2

Reaction notes

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