Water → Methyl 1-(3-chloropyridin-2-yl)-3-(hydroxymethyl)-1H-pyrazole-5-carboxylate

HRID 41860Notes

Reaction equation

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

Participants

Conditions

Temperature: -72 °C

Procedure

Under argon 12.3 g (41.7 mmol) of dimethyl 1-(3-chloropyridin-2-yl)-1H-pyrazole-3,5-dicarboxylate are introduced in 430 ml of tetrahydrofuran and this initial charge is cooled to −72° C. and admixed dropwise with 100 ml (100 mmol of a 1 M solution in hexane) of diisobutylaluminium hydride. The mixture is allowed to warm to 0° C. overnight and 65 ml of water are cautiously added. The solvents are removed on a rotary evaporator and the residue is extracted to exhaustion with methanol on a Soxhlet apparatus. Following removal of the solvent, the residue is purified on silica gel (cyclohexane/ethyl acetate=2:1→1:1).

Workup

additionthis initial charge
temperatureto warm to 0° C. overnight
customThe solvents are removed on a rotary evaporator
extractionthe residue is extracted to exhaustion with methanol on a Soxhlet apparatus
customremoval of the solvent
customthe residue is purified on silica gel (cyclohexane/ethyl acetate=2:1→1:1)

Sources & evidence

ORD record: ord-811464bf8fa74f269e534842f3887e4c
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536092B2

Reaction notes

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