Aluminium lithium hydride → {1-[4-(trifluoromethyl)phenyl]-1H-pyrazol-3-yl}-methanol

HRID 2194843Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

A 100 mL round-bottomed flask was charged with methyl 1-(4-(trifluoromethyl)phenyl)-1H-pyrazole-3-carboxylate 63 (0.800 g, 2.96 mmol) and 10 mL of THF. After being cooled to 0° C., lithium aluminum hydride (1.0 M solution in THF, 2.96 mL, 2.96 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 concentrated to give (1-(4-(trifluoromethyl)phenyl)-1H-pyrazol-3-yl)methanol 64.

Workup

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

Sources & evidence

ORD record: ord-3178c6c51e5a4970b521f3fe44f53d85
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08334317B2

Reaction notes

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