[CH:1](Br)=[CH2:2].[Mg].[Cl:5][C:6]1[CH:19]=[CH:18][C:9]([C:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)=[O:11])=[CH:8][CH:7]=1.[Cl-].[NH4+]>O1CCCC1.O>[Cl:5][C:6]1[CH:19]=[CH:18][C:9]([C:10]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)([OH:11])[CH:1]=[CH2:2])=[CH:8][CH:7]=1
A solution of vinylbromide (11.8 g, 110 mmol) in 40 ml tetrahydrofuran was added to a mixture of magnesium (2.79 g, 115 mmol) in 20 ml tetrahydrofuran under a nitrogen atmosphere at 50° to 60° C. After reflux for 1 h 3-(4-chlorobenzoyl)pyridine (21.8 g, 0.100 mol) in 100 ml tetrahydrofuran was added at 10° C. After stirring for 1 h a solution of 8 g ammonium chloride in 40 ml water was added and the mixture filtrated. The organic phase was dried over sodium sulphate and evaporated to give 29.4 g of a red oil containing 20% unreacted starting ketone. This crude product was used directly in the next step (Example C).
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