Triphenylphosphine → 6-[1-(1H-imidazol-1-ylmethyl)-2-methylpropoxy]-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1 (2H)-naphthalenone

Participants

Reaction Steps

Diethyl azodicarboxylate (0.16 mL, 0.99 mmol) was added over 10 min to a mixture of 6-Hydroxy-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1(2H)-naphthalenone (300 mg, 0.99 mmol), 1-(1H-imidazol-1-yl)-3-methyl-2-butanol (167 mg, 1.08 mmol), triphenylphosphine (259 mg, 0.99 mmol) and tetrahydrofuran (2 mL) under nitrogen. The resulting mixture was stirred for 3 d, whereupon it was concentrated and the residue was purified by dry-flash column chromatography (SiO2, 1-9% 2-propanol-dichloromethane) to give 6-[1-(1H-imidazol-1-ylmethyl)-2-methylpropoxy]-5-[(phenylsulfonyl)methyl]-3,4-dihydro-1 (2H)-naphthalenone as a colorless solid, 46 mg, 10% yield. NMR spectrum was consistent with structure. Calcd. for C25H28N2O4S.¼H2O: Theory: C, 65.69; H, 6.28; N, 6.13. Found: C, 65.77; H, 6.67; N, 6.11.

Provenance & Evidence