HCID 15644271, compound → HCID 10039450, compound

Participants

Reaction Steps

In a 5-L round bottomed flask equipped with a reflux condenser and an overhead stirrer was placed a solution of 276 3 g (1.35 mole) of 1-cyclobutyl-1-hydroxy-1-phenyl-2-propanone in 3 L of tetrahydrofuran. To this solution was added 903 g (1.82 mole) of pyrrolidone hydrotribromide. The mixture was refluxed for 24 hours and allowed to cool to room temperature. It was partitioned between 4 L of water and 4 L of ether. The organic layer was separated, washed three times with a saturated solution of sodium bicarbonate and once with brine. It was dried over anhydrous magnesium sulfate and the solvent removed. Crystallization of the residue from hexane gave 195 g of 3-bromo-1-cyclobutyl-1-hydroxy-1-phenyl -2-propanone, mp 79°-80° C. NMR (CDCl3) 1.8-2.2 (m, 6 H), 3.4-3.6 (m, 1 H), 3.9-4.1 (m, 2 H), 7.2-7.7 (m, 5 H); IR (KBr) 3471, 2946, 1725, 627 cm-1.

Provenance & Evidence