Sodium sulfate decahydrate → [5-isobutoxy-1-(2-methylphenyl)-1H-pyrazol-3-yl]methanol

HRID 507939Notes

Reaction equation

[CH2:1]([O:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[N:9]=[C:8]([C:18](OCC)=[O:19])[CH:7]=1)[CH:2]([CH3:4])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:1]([O:5][C:6]1[N:10]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[N:9]=[C:8]([CH2:18][OH:19])[CH:7]=1)[CH:2]([CH3:4])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution (10 mL) of ethyl 5-isobutoxy-1-(2-methylphenyl)-1H-pyrazole-3-carboxylate (1.07 g, 3.54 mmol) in anhydrous tetrahydrofuran was added lithium aluminum hydride (0.13 g, 3.54 mmol) under stirring at 0° C., and the mixture was stirred at the same temperature for 2 hr. After completion of the reaction, sodium sulfate decahydrate (2.28 g, 7.08 mmol) was added to the reaction system and the mixture was stirred at room temperature for 2 hr. The precipitated insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-1/1) to give the title compound (0.85 g, yield 92%) as a pale-yellow oil.

Workup

stirringthe mixture was stirred at the same temperature for 2 hr
additionwas added to the reaction system
stirringthe mixture was stirred at room temperature for 2 hr
filtrationThe precipitated insoluble material was filtered off
concentrationthe filtrate was concentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1-1/1)

Sources & evidence

ORD record: ord-d6648e58d64049e6820c08b7730e49c8
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786165B2

Reaction notes

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