Diphenyl Ether → Diisopropyl Ether

HRID 2104102Notes

Reaction equation

HRID 2104102 reaction equation
[C:1]1([O:7][C:8]2[CH:13]=CC=C[CH:9]=2)[CH:6]=CC=C[CH:2]=1.CC1(C)O[C:19](=[O:21])[C:18](=[CH:22][NH:23][C:24]2[S:25][CH:26]=[C:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:28]=2)C(=O)O1>>[CH:1]([O:7][CH:8]([CH3:13])[CH3:9])([CH3:6])[CH3:2].[C:29]1([C:27]2[C:28]3[C:19](=[O:21])[CH:18]=[CH:22][NH:23][C:24]=3[S:25][CH:26]=2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 684322042,2-Dimethyl-5-[(4-phenyl-thiophen-2-ylamino)-methylene]-[1,3]dioxane-4,6-dione

Product 2

HCID 7914Diisopropyl EtherHCID 684349933-phenyl-7H-thieno[2,3-b]pyridine-4-one

Procedure

Diphenyl ether (15 ml) was heated to reflux and 2,2-dimethyl-5-[(4-phenyl-thiophen-2-ylamino)-methylene]-[1,3]dioxane-4,6-dione (1.41 g, 4.29 mmol) was added in portions with evolution of gas. The reaction mixture was kept at reflux for a further 45 min, before cooling to room temperature. Trituration with diisopropyl ether and petroleum ether (40-60° ) gave 3-phenyl-7H-thieno[2,3-b]pyridine-4-one. Yield=0.7 g, (72%).

Workup

  1. temperatureto reflux
  2. temperatureat reflux for a further 45 min

Sources & evidence

ORD record
ord-7a8ff18c58664207adac3712488fe77f
Source dataset
uspto-grants-2009_08
Patent number
US07576212B2

Reaction notes

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