Aluminium lithium hydride → HCID 67259679, compound

HRID 79339Notes

Reaction equation

HRID 79339 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][N:8]2[C:12]([C:13](OCC)=[O:14])=[CH:11][CH:10]=[N:9]2)=[CH:5][CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]([CH2:13][OH:14])=[CH:11][CH:10]=[N:9]2)=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54208979ethyl 1-(4-methoxybenzyl)-1H-pyrazole-5-carboxylate

Product 1

HCID 67259679HCID 67259679, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To ethyl 1-(4-methoxybenzyl)-1H-pyrazole-5-carboxylate (1.81 g, 6.95 mmol) in THF (20 mL) at 0° C. was added lithium aluminum hydride (0.317 g, 8.34 mmol). The cold bath was removed. The reaction mixture was stirred for 5 hours, diluted with Et2O (50 mL) and Celite (5 g) was added to the reaction mixture. The mixture was cooled to 0° C. and sodium sulfate decahydrate was cautiously added to quench the reaction. The mixture was filtered and washed with EtOAc (100 mL). The solution was concentrated under reduced pressure to give the product (1.36 g).

Workup

  1. customThe cold bath was removed
  2. additiondiluted with Et2O (50 mL) and Celite (5 g)
  3. additionwas added to the reaction mixture
  4. additionsodium sulfate decahydrate was cautiously added
  5. customto quench
  6. customthe reaction
  7. filtrationThe mixture was filtered
  8. washwashed with EtOAc (100 mL)
  9. concentrationThe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e63722a65ef64491b462ae6f320ce308
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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