1,1-bis(4-methoxyphenyl)prop-2-yn-1-ol → HCID 21192141, compound

Participants

Reaction Steps

A solution of methyl 4-hydroxy-6-methoxy-2-naphthoate (1.0 g, 4.3 mmol) and 1,1-di(4-methoxyphenyl)prop-2-yn-1-ol (1.16 g, 4.3 mmol) in toluene (45 cm3) containing acidic alumina (Brockmann 1), (4.0 g) was refluxed for 45 minutes. The cooled solution was filtered and the alumina was washed well with EtOAc (200 cm3). The organic filtrate was washed with aqueous sodium hydroxide (2M, 2×50 cm3) and water (100 cm3). Removal of the dried (Na2SO4) EtOAc gave an oil which was flash chromatographed over silica using 25% EtOAc in hexane as the eluent to afford a pale yellow solid. Recrystallisation from EtOAc/hexane gave methyl 9-methoxy-2,2-bis(4-methoxyphenyl)-2H-naphtho[1,2-b]pyran-5-carboxylate (yield=0.79 g, theoretical yield=2.08 g 38%, m.p. 162.5-164.0° C. (uncorrected)).

Provenance & Evidence