Ethyl Acetate → HCID 19867638, compound

HRID 2293821Notes

Reaction equation

HRID 2293821 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:20][C:21](=O)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:9]([C:15](=O)[CH:16]([CH3:18])[CH3:17])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.Cl.[NH2:30]O.[NH4+].[OH-].CCOC(C)=O>CC(O)=O.O.CCCCCC>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:20]=[C:21]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:30]=[C:15]([CH:16]([CH3:18])[CH3:17])[C:9]=2[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 14923Ammonium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 86749404HCID 86749404, compound

Product 1

HCID 19867638HCID 19867638, compoundYield 65.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8058HexaneSolvent

Procedure

A mixture of β-(4-fluorophenyl)-α-(2-methyl-1-oxopropyl)-δ-oxobenzenepentanoic acid, ethyl ester (7.92 gm, 20.6 mmol) and hydroxylamine hydrochloride (4.32 gm, 62.2 mmol) in glacial HOAc (100 ml) was refluxed for 2.5 hours. The reaction was cooled to room temperature and poured into an ice cold solution of concentrated NH4OH (140 ml) in H2O (400 ml). The resulting mixture was extracted twice with Et2O and the combined ethereal layers were washed with brine, dried (Na2 SO4), filtered and stripped to yield a gummy orange-red oil. Flash chromatography of the oil (Merck SiO2, 7% EtOAc in hexane) gave 4-(4-fluorophenyl)-2-(1-methylethyl)-6-phenyl-3-pyridinecarboxylic acid, ethyl ester (4.88 gm, 65%) as a near colorless gum.

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. extractionThe resulting mixture was extracted twice with Et2O
  3. washthe combined ethereal layers were washed with brine
  4. customdried (Na2 SO4)
  5. filtrationfiltered
  6. customto yield a gummy orange-red oil

Sources & evidence

ORD record
ord-36ff69e158e44183a7264da5fda8b495
Source dataset
uspto-grants-1997_11
Patent number
US05686433

Reaction notes

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