Hydrochloric Acid → HCID 58020671, compound

HRID 1753098Notes

Reaction equation

HRID 1753098 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]([CH3:13])[CH3:12])[CH:10]=1)=O)C.CC(C[AlH]CC(C)C)C.Cl>C1(C)C=CC=CC=1>[CH:11]([N:9]1[CH:10]=[C:6]([CH2:4][OH:3])[C:7]([C:14]([F:17])([F:16])[F:15])=[N:8]1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14487Diisobutylaluminum hydrideHCID 57574507ethyl 1-isopropyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Product 1

HCID 58020671HCID 58020671, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1-Isopropyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid ethyl ester (Preparation 111, 10.2 g, 40.76 mmol) in toluene (200 mL) at −78° C. was added DIBALH (85 mL, 101.91 mmol) dropwise and the reaction allowed to stir at this temperature for 2 hours. 2N HCl was added to quench the reaction followed by extraction into EtOAc. The organic layer was collected, washed with water, brine, dried over sodium sulphate and concentrated in vacuo to afford the title compound (8.3 g) that was taken directly on to the next step.

Workup

  1. customto quench the reaction
  2. extractionfollowed by extraction into EtOAc
  3. customThe organic layer was collected
  4. washwashed with water, brine
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf82463c328c4e468a459fce93e2d4b2
Source dataset
uspto-grants-2015_10
Patent number
US09163021B2

Reaction notes

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