Aluminium lithium hydride → HCID 86662719, compound

HRID 2090924Notes

Reaction equation

HRID 2090924 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[C:12]([C:14](OC)=[O:15])[C:11]([CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[N:10]2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[C:12]([CH:14]=[O:15])[C:11]([CH2:18][N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[N:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66778357HCID 66778357, compound2×

Product 1

HCID 86662719HCID 86662719, compoundYield 70.1%

Reagents, catalysts & solvents 3

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution (20 mL) of methyl 1-(4-methoxyphenyl)-3-(morpholin-4-ylmethyl)-1H-pyrazole-4-carboxylate (11.3 g) synthesized in the above-mentioned (2) in tetrahydrofuran was added to an ice-cooled solution (80 mL) of lithium aluminum hydride (1.4 g) in tetrahydrofuran. The ice bath was removed, and the reaction mixture was stirred at room temperature for 1 hr. The mixture was ice-cooled again, and water (3.7 mL), 1N aqueous sodium hydroxide solution (18.5 mL) and water (3.7 mL) were successively added dropwise to quench the reaction. The residue was filtered through celite, and the filtrate was concentrated under reduced pressure to give a crude product (8.5 g) of 1-(4-methoxyphenyl)-3-(morpholin-4-ylmethyl)-1H-pyrazole-4-methanol as a pale-yellow oil. This was dissolved in toluene (150 mL), manganese dioxide (15 g) was added, and the mixture was heated for 30 min with a Dean-Stark trap. The reaction mixture was allowed to cool to room temperature, and manganese dioxide was collected by filtration. The solvent was evaporated under reduced pressure to give the title object compound (7.2 g, 70%) as a yellow oil.

Workup

  1. customThe ice bath was removed
  2. temperaturecooled again
  3. additionwater (3.7 mL), 1N aqueous sodium hydroxide solution (18.5 mL) and water (3.7 mL) were successively added dropwise
  4. customto quench
  5. customthe reaction
  6. filtrationThe residue was filtered through celite
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customto give a crude product (8.5 g) of 1-(4-methoxyphenyl)-3-(morpholin-4-ylmethyl)-1H-pyrazole-4-methanol as a pale-yellow oil
  9. temperaturethe mixture was heated for 30 min with a Dean-Stark trap
  10. temperatureto cool to room temperature
  11. filtrationmanganese dioxide was collected by filtration
  12. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-5c7c4e0fee7c4c87bca4fe89c7dae194
Source dataset
uspto-grants-2013_05
Patent number
US08436043B2

Reaction notes

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