Ethanol → HCID 86686309, compound

HRID 1043870Notes

Reaction equation

HRID 1043870 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:17][CH2:16][O:15][CH2:14]3)[N:11]=[CH:10][C:9]=2[C:18]([O:20]CC)=[O:19])=[C:4]([Cl:23])[CH:3]=1.[OH-].[Na+].C(O)C>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH:13]3[CH2:17][CH2:16][O:15][CH2:14]3)[N:11]=[CH:10][C:9]=2[C:18]([OH:20])=[O:19])=[C:4]([Cl:23])[CH:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 86686310HCID 86686310, compound

Product 1

HCID 86686309HCID 86686309, compoundYield 102.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of (±)-ethyl 5-(4-bromo-2-chlorophenyl)-1-(tetrahydrofuran-3-yl)-1H-pyrazole-4-carboxylate (1.05 g) and a 5 M aqueous sodium hydroxide solution (1.58 mL) was stirred in a mixed solvent of ethanol (20 mL) and water (5 mL) at 60° C. for three hours. The reaction mixture was cooled to room temperature and then concentrated under reduced pressure. 5 M hydrochloric acid was added to the residue, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the desiccant was filtered off. The filtrate was concentrated under reduced pressure to give the title compound (1 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. addition5 M hydrochloric acid was added to the residue
  3. extractionfollowed by extraction with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationthe desiccant was filtered off
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9a7579da52554de38eadb7f92dc28905
Source dataset
uspto-grants-2013_10
Patent number
US08563565B2

Reaction notes

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