Water → [1-(3-Fluoro-2-pyridyl)-3-(isopropoxymethyl)pyrazol-4-yl]methanol

HRID 1517575Notes

Reaction equation

[F:1][C:2]1[C:3]([N:8]2[CH:12]=[C:11]([C:13](OC(C)C)=[O:14])[C:10]([CH2:19][O:20][CH:21]([CH3:23])[CH3:22])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C.O1CCCC1>[F:1][C:2]1[C:3]([N:8]2[CH:12]=[C:11]([CH2:13][OH:14])[C:10]([CH2:19][O:20][CH:21]([CH3:23])[CH3:22])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of isopropyl 1-(3-fluoro-2-pyridyl)-3-(isopropoxymethyl)pyrazole-4-carboxylate (316 mg, 0.98 mmol) in diethyl ether (4.9 mL) under nitrogen and cooled to 0° C., 1M lithium aluminium hydride in tetrahydrofuran (1.2 mL) is added. The mixture is stirred at 0° C. for 1 hour. Water (46 μL) is added and stirred for 5 min, then 15% aqueous solution of NaOH (46 μL) and water (138 μL) are successively added. Solids are filtered and solvent evaporated to obtain 241 mg of [1-(3-fluoro-2-pyridyl)-3-(isopropoxymethyl)pyrazol-4-yl]methanol that is used without further purification. MS (m/z): 266 (M+1).

Workup

stirringstirred for 5 min
filtrationSolids are filtered
customsolvent evaporated

Sources & evidence

ORD record: ord-ff1db639244f4d4dba3c587d6d3c72d6
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232289B2

Reaction notes

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