Ethanol → HCID 23157311, compound

HRID 507968Notes

Reaction equation

HRID 507968 reaction equation
[CH3:1][O:2][C:3]1[CH:7]=[C:6]([C:8](OC)=[O:9])[N:5]([CH3:12])[N:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)C.[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:7]=[C:6]([CH2:8][OH:9])[N:5]([CH3:12])[N:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 12226057methyl 3-methoxy-1-methyl-1H-pyrazole-5-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 23157311HCID 23157311, compoundYield 98.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-methoxy-1-methyl-1H-pyrazole-5-carboxylate (2.03 g, 11.9 mmol) in tetrahydrofuran (20 mL) was added lithium aluminum hydride (0.57 g, 12 mmol) at 0° C., and the mixture was stirred at room temperature for 30 min. Ethanol (10 mL) and saturated aqueous ammonium chloride solution (2.0 mL) were added to the reaction mixture, and the precipitated solid was filtered off. The filtrate was concentrated and the residue was purified by silica gel column chromatography (ethyl acetate) to give the title compound (1.67 g, yield 98%) as a colorless oil.

Workup

  1. filtrationthe precipitated solid was filtered off
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by silica gel column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-934188aef16b4267888c93d1add8d5fc
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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