Tetrahydrofuran → HCID 22719305, compound

Participants

Reaction Conditions

Reaction Steps

0.7 g (1.3 mmol) 22, 0.15 g (1.44 mmol) 19 and 0.5 g activated molecular sieves (4 Å) were added to dry THF (10 ml). After the mixture was cooled to 0° C., 0.15 g (1.44 mmol) triethylamine was added. Then it was allowed to reach room temperature and was stirred for three hours. Ammonium salts were filtered off, the THF was evaporated and the crude product was redissolved in chloroform. The solution was extracted three times with diluted potassium hydroxide solution, two times with water, one time with brine and was then dried over magnesium sulfate. After the chloroform was evaporated, the monomer was purified by column chromatography on silica gel using 50% ethyl acetate in hexanes as eluent. The evaporation of the solvent yielded 0.4 g (51%) of a viscous dark orange oil. Rf=0.37 (EtOAc/hexanes: 1/1). 1H NMR (CDCl3, 500 MHz, 20° C.): d 8.99 (s, 1H), 8.85 (m, 2H), 8.74 (s, 1H), 6.10 (s, 1H), 5.56 (s, 1H), 4.60 (m, 2H), 4.28 (m, 2H), 3.88 (m, 2H), 3.71 (m, 10H), 1.93 (s, 3H). 13C NMR (CDCl3, 125 MHz, 20° C.): d 184.9, 162.6, 149.6, 146.8, 138.5, 138.4, 137.6, 136.2, 136.1, 135.5, 131.7, 129.3, 125.7, 125.3, 122.6, 70.7, 69.1, 68.8, 65.7, 63.8, 18.3.

Provenance & Evidence