Hydrochloric Acid → (1-Cyclopropyl-5-(trifluoromethyl)-1H-pyrazol-4-yl)methanol

HRID 1753088Notes

Reaction equation

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

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 1-cyclopropyl-5-trifluoromethyl-1H-pyrazole-4-carboxylic acid ethyl ester (Preparation 96, 1.4 g, 5.64 mmol) in dry toluene (25 mL) was cooled to −78° C. and DIBAL-H (11.8 mL of 1.2 M solution in toluene, 14.1 mmol) was added dropwise to it. The reaction mixture was stirred at −78° C. for 2 hours and poured into 2N HCl (10 mL). This was stirred for a further 4 hours at room temperature followed by extraction with EtOAc (2×25 mL) and the combined organic layers were washed with water (2×10 mL), brine (10 mL) dried (Na2SO4) and evaporated in vacuo to afford the title compound as off white solid (100%, 1.2 g).

Workup

stirringThis was stirred for a further 4 hours at room temperature
extractionfollowed by extraction with EtOAc (2×25 mL)
washthe combined organic layers were washed with water (2×10 mL), brine (10 mL)
dry with materialdried (Na2SO4)
customevaporated in vacuo

Sources & evidence

ORD record: ord-e1aafa374cc1419ab79964eff0e0930d
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09163021B2

Reaction notes

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