Dimethylformamide → Dimethyl-sulfamic acid 5-tert-butyl-4-{4-hydroxy-6,6-bis-[2-(4-hydroxy-phenyl)-ethyl]-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl}-2-methyl-phenyl ester

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Reaction Steps

To a round bottom flask equipped with a magnetic stirrer were added toluene-4-thiosulfonic acid S-(2-tert-butyl-4-dimethylsulfamoyloxy-5-methyl-phenyl) ester (prepared in Example UUU; 0.128 g, 0.280 mmol), 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), K2CO3 (0.154 g, 1.12 mmol), and DMF (8 mL), as described in General Method 9. The slurry was stirred at room temperature overnight. After standard work-up, the residue was submitted to flash chromatography (97% CHCl3 :3% MeOH) to yield the title compound, m.p. 139° C. 1H NMR (CDCl3) δ 1.53 (s, 9 H), 1.91 (s, 3 H), 2.11 (m, 4 H), 2.65 (m, 4 H), 2.86 (s, 2 H), 2.98 (s, 6 H), 4.80 (br s, 2 H), 6.72 (s, 1 H), 6.73 (d, 4 H), 6.98 (d, 4 H), 7.27 (s, 1 H).

Provenance & Evidence