Methallyl alcohol → HCID 17979065, compound

Participants

Reaction Steps

In 10 ml of tetrahydrofuran was suspended 0.19 g of sodium hydride (60% in oil), to which 0.5 ml of a solution containing 0.57 g of 2-pentyn-1-ol in tetrahydrofuran was added dropwise at room temperature, followed by stirring for 10 minutes. To this was added dropwise 0.4 ml of a solution con-taining 0.3 g of 4,6-dichloropyrimidin in tetrahydrofuran at 0° C., followed by stirring for 1 hour. To this was added dropwise 0.5 ml of a solution containing 0.48 g of 2-methyl-2-propen-1-ol in tetrahydrofuran at the same temperature and further added 0.19 g of sodium hydride (60% in oil), followed by stirring at 2 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 0.64 g of 4-(2-methyl-2-propenyloxy)-6-(2-pentynyloxy)pyrimidine.

Provenance & Evidence