Tetrahydrofuran → 7-Chloro-2,3-dihydro-5-(1-hydroxyethyl)-3-methyl-furo[2,3-c]pyridine

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Reaction Steps

A solution of 2-chloro-3-(1-propen-3-yl)-4-iodo-6-(1-hydroxyethyl)-pyridine (1.06 g, 3.14 mmol) in THF (5 mL) is treated with 50% hypophosphorous acid (2.13 g, 15.73 mmol), triethylamine (1.75 g, 17.33 mmol), and 2,2'-azobis(2-methylpropino-nitrile) (AIBN; 192 mg, 1.23 mmol). The solution is stirred at reflux for 2 hours. The solution is allowed to cool and concentrated in vacuo. Sat'd NaHCO3 is added, and the mixture is extracted 3× EtOAc. The organics are dried over MgSO4, and concentrated in vacuo. The crude light yellow oil is chromatographed (SiO2, hexane/ethyl acetate, 2:1) to yield 650 mg (97%) of 7-chloro-2,3-dihydro-5-(1-hydroxyethyl)-3-methyl-furo[2,3-c]pyridine, mp 67-68° C.

Provenance & Evidence