Benzyl Alcohol → benzyl N-(3-methylidenecyclobutyl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 26.7 g (238 mmol) of 3-methylenecyclobutane carboxylic acid (Cripps, H. N.; Williams, J. K.; Sharkey, W. H. J. Am. Chem. Soc. 1959, 81, 2723 2728) in 100 mL of toluene at 0° C. was added 36.4 mL (262 mmol) of triethylamine and then 72.1 g (262 mmol) of diphenylphosphoryl azide. The reaction mixture was then heated at 80° C., and after 1 h, 28.33 g (262 mmol) of benzyl alcohol was added. After 15 h at 85° C., the cooled reaction mixture was poured into 1 L of ether, washed with saturated aqueous NaHCO3, and then saturated aqueous NaCl, dried over MgSO4, and then concentrated under reduced pressure. Chromatography of the residue in three portions on 1400 g of silica gel with 80:20/hexane:EtOAc afforded 35.4 g (63%) of the desired compound. MS DCI/NH3M?Z: 218 (M+H)+, 235 (M+NH4)+ ;1H NMR (CDCl3) 2.60 (m, 2H), 3.05 (m, 2H), 4.20 (m, 1H), 4.83 (m, 2H), 5.21 (s, 2H), 7.45 (m, 5H).

Provenance & Evidence