Water → (3,5-dichloro-1-ethyl-1H-pyrazol-4-yl)methanol

HRID 1172112Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[C:12]([C:13](OCC)=[O:14])=[C:11]([Cl:18])[N:10]([CH2:19][CH3:20])[N:9]=1.C(OCC)(=O)C.O>O1CCCC1>[Cl:7][C:8]1[C:12]([CH2:13][OH:14])=[C:11]([Cl:18])[N:10]([CH2:19][CH3:20])[N:9]=1

Participants

Conditions

Temperature: -50 °C

Procedure

A solution of 0.16 g (4.2 mmoles) of lithium aluminum hydride dissolved in 70 ml of tetrahydrofuran was cooled to −50° C. Thereto was gradually added dropwise a solution of 1.0 g (4.2 mmoles) of ethyl 3,5-dichloro-1-ethyl-1H-pyrazole-4-carboxylate dissolved in 30 ml of tetrahydrofuran. The mixture was stirred at −50° C. for 3 hours to give rise to a reaction. After confirmation of the completion of the reaction, ethyl acetate was added, followed by stirring for a while. Water was added, followed by stirring for a while. The resulting mixture was filtered under vacuum. The filtrate was extracted with ethyl acetate. The resulting organic layer was washed with water and an aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to vacuum distillation to remove the solvent contained therein, to obtain 0.82 g (yield: 100%) of (3,5-dichloro-1-ethyl-1H-pyrazol-4-yl)methanol as a brown oily substance.

Workup

customto give rise
customto a reaction
additionwas added
stirringby stirring for a while
stirringby stirring for a while
filtrationThe resulting mixture was filtered under vacuum
extractionThe filtrate was extracted with ethyl acetate
washThe resulting organic layer was washed with water
dry with materialan aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate
distillationThe resulting solution was subjected to vacuum distillation
customto remove the solvent

Sources & evidence

ORD record: ord-5a53985284e64f679f43116d2a89b637
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07833939B2

Reaction notes

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