Hydrochloric Acid → (1-Cyclopropyl-3-(trifluoromethyl)-1H-pyrazol-4-yl)methanol

HRID 1753093Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:7]([C:14]([F:17])([F:16])[F:15])=[N:8][N:9]([CH:11]2[CH2:13][CH2:12]2)[CH:10]=1)=O)C.CC(C[AlH]CC(C)C)C.Cl>C1(C)C=CC=CC=1>[CH:11]1([N:9]2[CH:10]=[C:6]([CH2:4][OH:3])[C:7]([C:14]([F:17])([F:16])[F:15])=[N:8]2)[CH2:13][CH2:12]1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 1-Cyclopropyl-3-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (Preparation 101, 3.5 g, 14.11 mmol) in dry toluene (70 mL) was cooled to −78° C. and DIBAL-H (29.4 mL of a 1.2 M solution in toluene, 35.3 mmol) was added dropwise. The reaction mixture was stirred at −78° C. for 2 hours and then poured into 2N HCl (25 mL) followed by further stirring for 2 hours at room temperature. The mixture was extracted with EtOAc (2×50 mL) and the combined organic layers were washed with water (2×15 mL), brine (15 mL) and dried (Na2SO4) and evaporated in vacuo to afford the title compound as off white solid (100%, 3 g).

Workup

stirringby further stirring for 2 hours at room temperature
extractionThe mixture was extracted with EtOAc (2×50 mL)
washthe combined organic layers were washed with water (2×15 mL), brine (15 mL)
dry with materialdried (Na2SO4)
customevaporated in vacuo

Sources & evidence

ORD record: ord-02b34c30c3a04a00875cb5490469bcad
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163021B2

Reaction notes

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