p-tert-Butylphenyl glycidyl ether → HCID 23654788, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of spiro[naphtho[1,2-b][1,4]oxathiine-2,4′-piperidine]-5,6-dione (0.15 g, 0.5 mmol) in acetonitrile (3.0 mL) was added 2-[(4-tert-butylphenoxy)methyl]oxirane (0.11 g, 0.55 mmol) followed by lithium perchlorate (0.058 g, 0.55 mmol). The reaction mixture was stirred at 80° C. for 16 hours. The solvent was removed under vacuum. The crude product was purified by flash column chromatography (SiO2, 100% EtOAc to 2% methanol in EtOAc) to give the desired product as a purple solid (0.072 g, 29%). M.p.=137-140° C.; 400 MHz 1H NMR (CDCl3) δ: 8.05 (d, 1H), 7.75 (d, 1H), 7.65 (t, 1H), 7.5 (t, 1H), 7.35 (d, 2H), 6.9 (d, 2H), 4.15 (m, 1H), 4.0 (d, 2H), 2.95 (m, 3H), 2.8 (m, 2H), 2.65 (m, 2H), 2.55 (t, 2H), 2.15 (d, 2H), 1.9 (m, 2H), 1.3 (s, 9H); LCMS: 508 [M+H].

Provenance & Evidence