Phenol → (+/-)cis-1-(2-Benzylphenoxy)-2-tert-butoxycarbonylaminoindane

Participants

Reaction Steps

A solution of (±) N-tert-butoxycarbonyl-1,2-iminoindane (2.33 g, 10 mmol), 2-hydroxy diphenylmethane (1.84 g, 10 mmol) and pyridinium p-toluenesulfonate (50 mg) in chloroform (100 ml) was heated at reflux for 3 h. On cooling, the solution was washed sequentially with aq. NaHCO3, water and then brine. After drying over Na2SO4, solvents were removed in vacuo and the resultant brown oil subjected to column chromatography on silica gel eluting with 10% diethyl ether in hexanes to afford a pale yellow oil which was a mixture of the desired adduct and the starting phenol. This mixture was taken up in 1:1 diethyl ether:pentane (200 ml) and washed three times with a 1:1 mixture of methanol and 10% aq. NaOH. After washing with water then brine, the organics were dried over Na2SO4 and then concentrated in vacuo. The residue was recrystallised to afford the title compound as a white solid (1.03 g) m.p. 113°-114.5° C. (from diethyl ether-pentane).

Provenance & Evidence