[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=2[Cl:16])[OH:8])[CH:2]=1.O1C[CH2:20][CH2:19][CH2:18]1.[H-].[Na+].C(Br)C=C>O>[CH2:20]([O:8][CH:7]([C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1)[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[Cl:16])[CH:19]=[CH2:18]To a 250 ml single neck round bottom flask equipped with a reflux condensor and an argon inlet was added 3.56 gm of the 3-pyridyl-2,4-dichlorophenylcarbinol and 60 ml of anhydrous tetrahydrofuran. The system was cooled to 0° C. and after cooling 0.37 gm sodium hydride added. The system was stirred for 75 additional minutes and 1.45 ml of allyl bromide was then added. The system was allowed to come to room temperature over 1/2-hour and stirred there for an additional 1 hour. Afterwards the system was heated at reflux for 18 hours. At this time, water was added to the system and the product extracted with methylene chloride. The methylene chloride was then washed with water and then dried over sodium sulfate. The methylene chloride was removed by stripping to give 1.73 gm of the 3-pyridyl-2,4-dichlorophenylcarbinol allylether and listed as compound number 3 in Table I.
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