Potassium Sodium Tartrate → (1-(propan-2-yl)-1H-pyrazol-3-yl)methanol

HRID 706588Notes

Reaction equation

[CH:1]([N:4]1[CH:8]=[CH:7][C:6]([C:9](OCC)=[O:10])=[N:5]1)([CH3:3])[CH3:2].[Al].[Li].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(OCC)C.O1CCCC1>[CH:1]([N:4]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[N:5]1)([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

Commercially available ethyl 1-isopropyl-1H-pyrazole-3-carboxylate was dissolved in diethyl ether, the solution was cooled to 0° C., and a 1M lithium aluminum solution in tetrahydrofuran was added. After stirring for 3 hours, the reaction mixture was poured into a cold 30% aqueous Rochelle's salt solution and was allowed to stir for one hour. The resulting mixture was extracted twice with diethyl ether. The combined organic extracts were washed with 10% aqueous potassium carbonate solution and brine, dried over sodium sulfate, and concentrated under reduced pressure to yield the desired compound (54% yield).

Workup

stirringto stir for one hour
extractionThe resulting mixture was extracted twice with diethyl ether
washThe combined organic extracts were washed with 10% aqueous potassium carbonate solution and brine
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-d567bbe7504a457190e71362a7d54f70
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174981B2

Reaction notes

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