Methyl butyrate → Methyl 2-ethyl-6-[(4,6-diphenyl-2-pyridyl)oxy]hexanoate

HRID 2396528Notes

Reaction equation

[C:1]1([C:7]2[CH:12]=[C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:10][C:9](=[O:19])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(OC)(=O)CCC.Br[CH2:28][CH2:29][CH2:30][CH2:31][CH:32]([CH2:37][CH3:38])[C:33]([O:35][CH3:36])=[O:34]>C(=O)([O-])[O-].[Ag+2].CN(C)C=O>[CH2:37]([CH:32]([CH2:31][CH2:30][CH2:29][CH2:28][O:19][C:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH:12]=[C:11]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:10]=1)[C:33]([O:35][CH3:36])=[O:34])[CH3:38]

Participants

Conditions

Temperature: 100 °C

Procedure

The procedure in Example 5 is followed but using 4,6-diphenyl-2-pyridinone (2.8 g) (prepared by analogy with the method described in Patent EP 108 592 from methyl butanoate), methyl 6-bromo-2-ethylhexanoate (5.4. g), silver carbonate (1.6 g) and dimethylformamide (100 cc). The reaction mixture is heated at 100° C. for 31 hours then at 120° C. for 40 hours. The product is purified by chromatography under pressure on silica gel (30-60 mm; eluent: n-hexane-ethyl acetate 9-1). (yellow oil)

Workup

customprepared by analogy with the method
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-936ea102adea4787876ed747b7604dca
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05492915

Reaction notes

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