Tetrahydrofuran → 1469286-32-5

HRID 931073Notes

Reaction equation

HRID 931073 reaction equation
[N:1]1([C:6]2([C:10]([O:12]CC)=[O:11])[CH2:9][CH2:8][CH2:7]2)[CH:5]=[CH:4][CH:3]=[N:2]1.O1CCCC1.[OH-].[Na+]>O>[N:1]1([C:6]2([C:10]([OH:12])=[O:11])[CH2:7][CH2:8][CH2:9]2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 89853540HCID 89853540, compound

Product 1

HCID 898542991469286-32-5Yield 18.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To ethyl 1-(1H-pyrazol-1-yl)cyclobutanecarboxylate (688 mg, 3.54 mmol) were added tetrahydrofuran (8 mL) and water (0.9 mL). Aqueous sodium hydroxide (1N, 4 mL, 4 mmol) was added to the mixture. The reaction mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure and to the residue was added aqueous hydrochloric acid (1N, 1 mL). The mixture was extracted with dichloromethane (3×). The combined organics were dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford the title compound (108.9 mg). The material was used without further purification.

Workup

  1. customThe solvent was removed under reduced pressure and to the residue
  2. additionwas added aqueous hydrochloric acid (1N, 1 mL)
  3. extractionThe mixture was extracted with dichloromethane (3×)
  4. dry with materialThe combined organics were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-16f5c9efd5a349688e59bd5abc6c5a17
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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