Reaction Steps
To a solution of epoxide (2C) (0.494 g, 1.73 mmol) in 7 ml of chloroform was added 3.5 ml of trifluoroacetic acid. The solution was refluxed for 2 hrs. under argon, and then allowed to stand at room temperature overnight. The solution was once again refluxed for 1 hr. and then allowed to cool to room temperature. Washing the solution with 10 ml of water, drying over sodium sulfate, and evaporating the solvent yielded a yellow oil. Subjecting the product to medium pressure liquid chromatography using hexane-ethyl acetate::7.:3 yielded 0.250 g (51%) of the β-tetralone 44:mp 88°-89° C. 1H NMR (CDCl3) δ2.43 (2H, t, J=6 Hz,ArCH2CH2CO), 2.96, (2H, t, J=6 Hz, ArCH2CH2), 3.50 (2H, ArCH2CO,s), 3.70 (3H, s, ArOCH3), 3.73 (3H, s, ArOCH3), 6.76 (1H, s, ArH); IR (CHCl3) 3030, 2980, 2905, 2840, 2400, 2250, 1780, 1710, 1575, 1510, 1470, 1430, 1400, 1375 (sh), 1335, 1285, 1210 (br), 1170 (sh), 1140, 1080, 1040, 1010 cm-1 etc.; mass spectrum m/e/ (rel. intensity) 286 (M+ +2, 100%), 284 (M+, 100%), 271 (M+ +2-CH3. 25%), 269 (M+ -CH3, 25%), 244 (M+ +2-CH2 =C=O, 31%), 242 (M+ -CH2 =C=O, 38%), 229 (M+ +2,CH3 --CH2 =C=0, 69%), 277 (M+ -CH3 -CH2 =C=O, 69%), etc.
