Dimethylformamide → Ethylsulfamic acid 5-tert-butyl-4-{4-hydroxy-6,6-bis-[2-(3-hydroxyphenyl)ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methylphenyl ester

Participants

Reaction Steps

To a round bottom flask equipped with a magnetic stirrer were added 4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-5,6-dihydro-pyran-2-one (prepared in Example PP; 0.100 g, 0.280 mmol), toluene-4-thiosulfonic acid S-(2-tert-butyl-4-ethylsulfamoyloxy-5-methyl-phenyl) ester (prepared in Example VVV; 0.128 g, 0.280 mmol), K2CO3 (0.154 g, 1.12 mmol), and DMF (8 mL), as described in General Method 9. The reaction was stirred at room temperature for 2 hours and then worked up in the usual manner. The residue was submitted to flash chromatography (95% CHCl3 :5% MeOH). The product obtained was taken up in a small amount of EtOAc, triturated with hexane, filtered and dried overnight under high vacuum to yield the title compound, m.p. 130° C. (dec.). 1H NMR (CDCl3) δ 1.22 (t, 3 H), 1.52 (s, 9 H), 1.92 (s, 3 H), 2.11 (m, 4 H), 2.66 (m, 4 H), 2.87 (s, 2 H), 3.31 (m, 2 H), 4.52 (br t, 1 H), 4.78 (br s, 2 H), 6.73 (d, 4 H), 6.98 (d, 4 H), 7.25 (s, 1 H), 7.70 (s, 1 H).

Provenance & Evidence