Hydrochloric Acid → (1-Isopropyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)methanol
Reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH:11]([N:14]1[C:18]([C:19]([F:22])([F:21])[F:20])=[C:17]([C:23](OCC)=[O:24])[CH:16]=[N:15]1)([CH3:13])[CH3:12].Cl>C1(C)C=CC=CC=1>[CH:11]([N:14]1[C:18]([C:19]([F:21])([F:20])[F:22])=[C:17]([CH2:23][OH:24])[CH:16]=[N:15]1)([CH3:13])[CH3:12]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Diisobutylaluminium hydride (99 mL, 120 mmol, 1.2 M solution in toluene) was added to ethyl 1-isopropyl-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate (WO 2007071900, 12 g, 48 mmol) in toluene (220 mL) at −78° C. The reaction mixture was stirred at −78° C. for 2 hours then poured into aqueous HCl (100 mL, 2 M). The mixture was stirred for 4 hours at room temperature then extracted with EtOAc (400 mL). The organic phase was washed with water (200 mL), brine (200 mL) and dried over sodium sulphate. The filtrate was evaporated in vacuo to afford the title compound as a colourless oil in 100% yield, 10.5 g.
Workup
- stirringThe mixture was stirred for 4 hours at room temperature
- extractionthen extracted with EtOAc (400 mL)
- washThe organic phase was washed with water (200 mL), brine (200 mL)
- dry with materialdried over sodium sulphate
- customThe filtrate was evaporated in vacuo
Sources & evidence
- ORD record
- ord-6d23c0c9a3744a8ab46f1b720b64ba44
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08846698B2
Reaction notes
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