4-(3,4-Methylenedioxyphenyl)-6-phenyl-2-pyridinone → Ethyl 2-methyl-6-{[4-(3,4-methylenedioxyphenyl)-6-phenyl-2-pyridyl]oxy}hexanoate

HRID 2396532Notes

Reaction equation

[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([C:10]3[CH:15]=[C:14]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[NH:13][C:12](=[O:22])[CH:11]=3)=[CH:4][C:3]=2[O:2]1.Br[CH2:24][CH2:25][CH2:26][CH2:27][CH:28]([CH3:34])[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C(=O)([O-])[O-].[Ag+2].CN(C)C=O>[CH3:34][CH:28]([CH2:27][CH2:26][CH2:25][CH2:24][O:22][C:12]1[CH:11]=[C:10]([C:5]2[CH:6]=[CH:7][C:8]3[O:9][CH2:1][O:2][C:3]=3[CH:4]=2)[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:13]=1)[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

Conditions

Temperature: 100 °C

Procedure

The procedure in Example 5 is followed but using 4-(3,4-methylenedioxyphenyl)-6-phenyl-2-pyridinone (2.5 g), ethyl 6-bromo-2-methylhexanoate (4 g), silver carbonate (1.2 g) and dimethylformamide (100 cc). The reaction mixture is heated at 100° C. for 72 hours. The product is purified by chromatography under pressure on silica gel (30-60 mm; eluent: n-hexane-ethyl acetate 9-1). (yellowish oil)

Workup

customThe product is purified by chromatography under pressure on silica gel (30-60 mm; eluent: n-hexane-ethyl acetate 9-1)

Sources & evidence

ORD record: ord-a5548e69b31f48139d45d1a927f4790b
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05492915

Reaction notes

Loading…