Benzeneacetic acid, alpha-methyl-, ethyl ester → 3-(4-Nitro-phenyl)-5-phenyl-isoxazole-4-carboxylic acid ethyl ester

HRID 75771

Reaction equation

HRID 75771 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.C(OC(=O)[CH:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH3:19])C.[CH2:27]([O:29][C:30](C1ON=C(C2C=CC([N+]([O-])=O)=CC=2)C=1)=[O:31])[CH3:28]>>[CH2:27]([O:29][C:30]([C:19]1[C:3]([C:4]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=2)=[N:2][O:1][C:18]=1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:31])[CH3:28]

Participants

4

Reactant 3

HCID 99643Benzeneacetic acid, alpha-methyl-, ethyl esterHCID 915274alpha-Chloro-4-nitrobenzaldoximeHCID 9493753-(4-Nitro-phenyl)-isoxazole-5-carboxylic acid ethyl ester

Product 1

HCID 673532643-(4-Nitro-phenyl)-5-phenyl-isoxazole-4-carboxylic acid ethyl ester

Conditions

Temperature
80 °C

Procedure

The title compound was prepared from N-hydroxy-4-nitro-benzimidoyl chloride and phenyl propionic acid ethyl ester by the same procedure as described for the synthesis of 3-(4-nitro-phenyl)-isoxazol-5-carboxylic acid ethyl ester in Example 1. The reaction mixture was refluxed for 16 hours instead of heating at 80° C. for 2.5 hours. The crude product was purified by flash chromatography over silica gel with 10-30% EtOAc in light petroleum to give the title compound in 40% yield. 1H NMR (DMSO-d6) δ: 0.98 (t, 3H), 4.11 (q, 2H), 7.53-7.61 (m, 3H), 7.87-7.93 (m, 4H), 8.32 (d, 2H); Mass (ES+), 339 (M++1).

Workup

  1. temperatureThe reaction mixture was refluxed for 16 hours instead
  2. customThe crude product was purified by flash chromatography over silica gel with 10-30% EtOAc in light petroleum

Sources & evidence

ORD record
ord-23d7dbfb5262467b81a3d4fd7aebb6e2
Source dataset
uspto-grants-2014_09
Patent number
US08835428B2

Linked notes

Loading…