Sodium Hydroxide → (1-cyclohexyl-1H-pyrazol-4-yl)methanol

HRID 2261316Notes

Reaction equation

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

Participants

Conditions

Temperature: 0 °C

Procedure

Under a nitrogen atmosphere, 0.57 g of lithium aluminum hydride was suspended in 100 ml of dry tetrahydrofuran, and a solution of 3.01 g of methyl 1-cyclohexyl-1H-pyrazole-4-carboxylate in 40 ml of tetrahydrofuran was added dropwise thereto over 15 minutes with stirring at 0° C. After completion of the addition, the mixture was stirred at room temperature for 7 hours and then cooled to 0° C. Thereto 10 ml of a 1 mol/L aqueous saturated sodium hydroxide solution was added dropwise. Produced precipitates were filtered and then washed with tetrahydrofuran. The filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 1.68 g of (cyclohexyl-1H-pyrazol-4-yl)methanol.

Workup

additionAfter completion of the addition
stirringthe mixture was stirred at room temperature for 7 hours
temperaturecooled to 0° C
customProduced
customprecipitates
filtrationwere filtered
washwashed with tetrahydrofuran
concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-c373739d292d4b4a9894d60fa93c41ce
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07846956B2

Reaction notes

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