Lithium Hydroxide → HCID 69297592, compound

HRID 1930351Notes

Reaction equation

HRID 1930351 reaction equation
[Li+].[OH-].[C:3]([C:7]1[CH:11]=[C:10]([C:12]([O:14]CC)=[O:13])[N:9]([CH:17]([CH3:19])[CH3:18])[N:8]=1)([CH3:6])([CH3:5])[CH3:4]>O.C1COCC1>[C:3]([C:7]1[CH:11]=[C:10]([C:12]([OH:14])=[O:13])[N:9]([CH:17]([CH3:19])[CH3:18])[N:8]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69036266HCID 69036266, compound

Product 1

HCID 69297592HCID 69297592, compoundYield 97.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution comprised of LiOH (2.3 g, 9 mmol) in water (12 mL) was added to a solution of ethyl 3-tert-butyl-1-isopropyl-1H-pyrazole-5-carboxylate (2.3 g, 9 mmol) in THF (24 mL) and the reaction mixture was heated to 50° C. overnight. The reaction was concentrated under reduced pressure and diluted with water. The solution pH was adjusted to pH 5 and the solution was extracted with EtOAc. The organics were washed with water and brine, dried (MgSO4) and concentrated under reduced pressure to give 3-tert-butyl-1-isopropyl-1H-pyrazole-5-carboxylic acid (1.85 g, 93% yield). 1H NMR (300 MHz, DMSO-d6): 6.62 (s, 1 H), 5.37 (m, 1 H), 1.35 (d, J=6.6 Hz, 6 H), 1.22 (s, 9 H). MS (ESI) m/z: (M+H+) 211.2

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additiondiluted with water
  3. extractionthe solution was extracted with EtOAc
  4. washThe organics were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a7fb685a8b2c442393e6e1b52cf89623
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

Loading…