6-Hydroxyquinoline → HCID 13663813, compound

Participants

Reaction Steps

A mixture of 1-adamantanemethanol (5.00 g, 30.0 mmol) and 6-hydroxyquinoline (13.1 g, 90.2 mmol) in tetrahydrofuran (75 mL) was stirred for 15 min. Then, triphenylphosphine (10.2 g, 39.0 mmol) was added, followed by diethyl azodicarboxylate (6.14 mL, 39.0 mmol). The reaction mixture was refluxed for 18 h. The solvent was then removed by rotary evaporation. The resulting gel was filtered through paper with diethyl ether (3×25 mL). The filtrate was rotary evaporated, and the resulting gel was filtered through paper with hexanes (3×25 mL). Again the filtrate was rotary evaporated, the resulting gel was filtered through paper with hexanes (3×25 mL), and the filtrate was rotary evaporated. This provided 3.8 g (43%) of crude product as a red oil. This oil was chromatographed (2:1 hexanes/ethyl acetate) to provide 1.6 g (18%) of (94):

Provenance & Evidence