Pyridine → HCID 13341362, compound

Participants

Reaction Steps

Into 40 ml of dried pyridine, was dissolved 6.6 g of 2-(1-methyl-1-hydroxyethyl)-2,3-dihydrobenzofuran. To the solution, with ice-cooling, was added dropwise 11.38 g of phosphorus oxychloride over a period of 10 minutes. After the addition was finished, the mixture was stirred for 2 hours at room temperature and poured into ice water. After ether was added to the mixture, the ether layer was separated and the aqueous layer was extracted twice with 50 ml of ether. The ether layers were combined, washed successively with 5% aqueous hydrochloric acid solution, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain 5.7 g of the crude 2-isopropylidene-2,3-dihydrobenzofuran. This crude product contained 2-isopropylbenzofuran, 2-isopropenyl-2,3-dihydrobenzofuran and small amount of many other unidentifiable impurities, in addition to the intended product. However, because of labileness of the intended product, the crude product was used in the starting material without further purification in the next preparative step.

Provenance & Evidence