Methanol → HCID 43328696, compound

HRID 1520781Notes

Reaction equation

HRID 1520781 reaction equation
[F:1][CH:2]([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][C:12]([C:15]([O:17]CC)=[O:16])=[N:11]2)=[CH:6][CH:5]=1.CO.O>C1COCC1>[F:20][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH:14]=[CH:13][C:12]([C:15]([OH:17])=[O:16])=[N:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 962WaterHCID 71087792HCID 71087792, compound

Product 1

HCID 43328696HCID 43328696, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of ethyl 1-(4-(difluoromethoxy)phenyl)-1H-pyrazole-3-carboxylate (350 mg, 1.24 mmol) in a mixture of THF (3.1 ml), methanol (1.6 ml), Water (1.6 ml) lithium hydroxide hydrate (89 mg, 3.72 mmol) was added. The solution was heated to 80° C. for 2 h. Most of the organic solvent was removed under reduced pressure. Sodium bicarbonate solution and ethyl acetate were added and the organic layer was separated. The aqueous layer was made acid by addition of 25% aqueous hydrochloric acid and the mixture was extracted 2 times with ethyl acetate. The organic layers were combined, dried (MgSO4) and evaporated. The product was dried in vacuo and was directly used for the next step.

Workup

  1. additionwas added
  2. customMost of the organic solvent was removed under reduced pressure
  3. additionSodium bicarbonate solution and ethyl acetate were added
  4. customthe organic layer was separated
  5. additionby addition of 25% aqueous hydrochloric acid
  6. extractionthe mixture was extracted 2 times with ethyl acetate
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe product was dried in vacuo

Sources & evidence

ORD record
ord-daedeb04994f4083a4f1ed920278b9aa
Source dataset
uspto-grants-2015_07
Patent number
US09073911B2

Reaction notes

Loading…