Tetrahydrofuran → HCID 17817484, compound

HRID 1356445Notes

Reaction equation

HRID 1356445 reaction equation
[C:1]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:13](=[O:14])[CH:12]=[CH:11][C:10]([C:15]([O:17]C)=[O:16])=[CH:9]2)=[CH:3][CH:2]=1.C1COCC1.[OH-].[Na+]>CO>[C:1]1([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:2]=[CH:3][C:4]([CH2:7][N:8]2[C:13](=[O:14])[CH:12]=[CH:11][C:10]([C:15]([OH:17])=[O:16])=[CH:9]2)=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 18508338HCID 18508338, compound

Product 1

HCID 17817484HCID 17817484, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 1-(4-biphenylylmethyl)-1,6-dihydro-6-oxo-3-pyridinecarboxylate (4.5 g) in methanol (50 ml)/THF (50 ml) was added dropwise 1N aqueous sodium hydroxide (28 ml) at room temperature. The reaction mixture was stirred at room temperature for 3 hr and concentrated. The residue was diluted with 1 N hydrochloric acid (30 ml) and extracted with a mixed solvent of ethyl acetate and THF. The organic layer was washed with saturated aqueous sodium chloride, dried, and concentrated. Diisopropylether was added to the residue and the resulting crystals were collected by filtration to obtain the titled compound (4.2 g).

Workup

  1. concentrationconcentrated
  2. additionThe residue was diluted with 1 N hydrochloric acid (30 ml)
  3. extractionextracted with a mixed solvent of ethyl acetate and THF
  4. washThe organic layer was washed with saturated aqueous sodium chloride
  5. customdried
  6. concentrationconcentrated
  7. additionDiisopropylether was added to the residue
  8. filtrationthe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-c813a12f1f4a4663aab1d90271e9cff9
Source dataset
uspto-grants-2003_07
Patent number
US06586475B1

Reaction notes

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