Phthalimide → Phthalimide, N-(3-methyl-2-butenyl)-

Participants

Reaction Steps

Phthalimide, potassium salt (20.5 g, 0.11 mol) was suspended in dry DMF (100 mL). To the suspension was added 1-bromo-3-methyl-2-butene (14.8 g, 0.1 mol) with stirring. The reaction mixture was stirred under N2 at 45° C. for 24 h. TLC (silica gel, 30% ethyl acetate-hexane) showed one major UV-visible spot with Rf =0.65. DMF was removed under vacuum and the residue was taken up with water (200 mL) and extracted with ethyl acetate (3×150 mL). The extracts were combined and dried over Na2SO4. Evaporation of solvent gave the title product as a white solid. Yield: 21.0 g (98%). mp: 95°-97° C. MS: 233 (M+NH4)+, 216 (M+H)+. 1H NMR (CDCl3) ε 1.71 and 1.83 [s, 6H, C(CH3)2 ], 4.26 (d, J=6.6 Hz, 2H, CH2CH=), 5.30 (t, 1H, CH=), 7.67 to 7.86 (m, 4H, Aromatic-H).

Provenance & Evidence