Aluminium lithium hydride → HCID 58360630, compound

HRID 2194848Notes

Reaction equation

HRID 2194848 reaction equation
[CH3:1][O:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:6]=[C:5]([C:18](OC)=[O:19])[CH:4]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:1][O:2][C:3]1[N:7]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:17])([F:15])[F:16])=[CH:12][CH:13]=2)[N:6]=[C:5]([CH2:18][OH:19])[CH:4]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67319803HCID 67319803, compound

Product 1

HCID 58360630HCID 58360630, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A 100 mL round-bottomed flask was charged with methyl 5-methoxy-1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxylate 72 (5.20 g, 17 mmol) and 100 mL of THF. After being cooled to 0° C., lithium aluminum hydride (1.0 M solution in THF, 17 mL, 17 mmol) was added dropwise. After 1 h, the reaction was quenched with 0.5 mL of water, 0.5 mL of 1 M NaOH, and 1.5 mL of water (added in that order). The resulting precipitate was filtered and the filtrate was concentrated to give (5-methoxy-1-(4-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)methanol 73.

Workup

  1. customthe reaction was quenched with 0.5 mL of water, 0.5 mL of 1 M NaOH, and 1.5 mL of water (
  2. additionadded in that order)
  3. filtrationThe resulting precipitate was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e548445472174bfc957450f64732fa63
Source dataset
uspto-grants-2012_12
Patent number
US08334317B2

Reaction notes

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