Isopropyl iodide → HCID 54272250, compound

Participants

Reaction Steps

To sodium hydride (2.84 g, 57% in oil, washed with pentane), 110 ml dry THF and 20 ml HMPT, cooled to 0° and under nitrogen, is added 12.7 g ethyl 4-phenyl-3-butenoate slowly with stirring. Then 6.5 ml of isopropyliodide is added and the reaction mixture is stirred for about 60 hrs. The reaction is worked up by extracting into water/ether mixture. The aqueous phase is extracted with ether. The organic phases are combined, washed with brine, dried over calcium sulfate and rotoevaporated to give ethyl 2-isopropyl-4-phenyl-3-butenoate, which is hydrolyzed (potassium hydroxide, water-methanol) to the acid, 2-isopropyl-4-phenyl-3-butenoic acid. The acid is reacted with m-phenoxybenzyl alcohol following the procedure of Example 4 to yield m-phenoxybenzyl ester of 2-isopropyl-4-phenyl-3-butenoic acid. NMR (CDCl3) δ0.91 [d, 3, J=Hz, --CH(CH3)2 ], 0.94 [d, 3, J=Hz, --CH(CH3)2 ], 5.13 (s, 2, benzyl), and 6.0-6.5 ppm (complex, 2, vinyl). IR (CCl4) 1745 cm-1 (C=O).

Provenance & Evidence