Sodium Hydroxide → HCID 23112894, compound

HRID 1180512Notes

Reaction equation

HRID 1180512 reaction equation
[C:1]1([N:7]2[C:15]3[CH2:14][CH2:13][CH2:12][CH:11]([CH2:16][C:17](OCC)=[O:18])[C:10]=3[CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Li+].[Al+3].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1>[C:1]1([N:7]2[C:15]3[CH2:14][CH2:13][CH2:12][CH:11]([CH2:16][CH2:17][OH:18])[C:10]=3[CH:9]=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 23112896ethyl 2-(4,5,6,7-tetrahydro-1-phenyl-1H-indazol-4-yl)acetate

Product 1

HCID 23112894HCID 23112894, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of ethyl 2-(4,5,6,7-tetrahydro-1-phenyl-1H-indazol-4-yl)acetate (1.40 g, 5.79 mmol) in 5 mL of THF is added over an aluminium-lithium hydride stirred suspension (300 mg, 7.9 mmol) in 20 mL of THF at room temperature. The mixture is maintained under stirring at room temperature for 18 hours and is afterwards refluxed during 1 hour. The mixture is hydrolyzed with ice and NaOH (10%), filtered through Celite and the solvent is evaporated under reduced pressure, to obtain 2-(4,5,6,7-tetrahydro-1-phenyl-1H-indazol-4-yl)ethanol (1.10 g, 4.55 mmol, 79%, oil)

Workup

  1. temperatureThe mixture is maintained
  2. temperatureis afterwards refluxed during 1 hour
  3. filtrationfiltered through Celite
  4. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-7e0942ed3b074a319df6d8edb34b29a7
Source dataset
uspto-grants-2007_10
Patent number
US07282499B2

Reaction notes

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