Tetrahydrofuran → 2-(2-Chlorobenzoyl)pyrimidine

反応式

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:11]1[N:16]=[CH:15][CH:14]=[CH:13][N:12]=1)C#N.[H-].[Na+].[O:19]1CCCC1>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:11]1[N:16]=[CH:15][CH:14]=[CH:13][N:12]=1)=[O:19]

参加物

反応物 3

HCID 8028Tetrahydrofuran

HCID 24758Sodium hydride

HCID 123729682-Chlorophenyl-(2-pyrimidinyl)acetonitrile

生成物 1

HCID 123729762-(2-Chlorobenzoyl)pyrimidine収率 64.7%

実験手順

A mixture of 2-chlorophenyl(2-pyrimidinyl)acetonitile (3.25 g, 0.0142 mol), sodium hydride (60% in mineral oil, 1.07 g, 0.016 mol) and anhydrous tetrahydrofuran is stirred two hours at reflux and cooled to room temperature. Dry air is bubbled into the mixture while stirring three days. The mixture is quenched by dropwise addition of a 3:1 water:methanol mixture and then water. The tetrahydrofuran is removed in vacuo and the aqueous residue filtered to afford the title compound as a brown solid (2.00 g, 64.7%) which is identified by NMR spectral analysis.