2-Butyn-1-ol → HCID 17979082, compound

Participants

Reaction Steps

In 3 ml of tetrahydrofuran was suspended 0.09 g of sodium hydride (60% in oil), to which 0.4 ml of a solution containing 0.31 g of 1,1-dichloro-3,3-dimethyl-2-butanol was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution containing 0.27 g of 4,6-dichloropyrimidine in tetrahydrofuran at 0° C., followed by stirring at the same temperature for 2.5 hours. To this was added dropwise 0.4 ml of a solution containing 0.15 g of 2-butyn-1-ol in tetrahydrofuran at room temperature and further added 0.09 g of sodium hydride (60% in oil), followed by stirring for 4 hours. The reaction mixture was then poured into a saturated aqueous ammonium chloride solution, which was extracted three times with t-butyl methyl ether. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to silica gel column chromatography to give 0.45 g of 4-(2-butynyloxy)-6-(1-(dichloromethyl)-2,2-dimethylpropyloxy)pyrimidine (the present compound (39)).

Provenance & Evidence