Isopropyl iodide → 7-Isopropyl-5-[isopropyl-(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran

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Reaction Steps

Following general procedure L and using 7-isopropyl-5-[(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran (Compound 52, 0.6 g, 2.7 mmol), 1.6M solution of n-butyllithium in hexanes (2.2 mL, 3.5 mmol) and 2-iodopropane (0.9 g, 5.4 mmol) in 10mL of anhydrous tetrahydrofuran, the title compound (0.077 g, 7%) was obtained as a brown oil after separation from recovered 7-isopropyl-5-[(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran (Compound 52, 0.2 g) by preparative normal phase HPLC using 4% ethyl acetate in hexanes as the mobile phase. 1H NMR (300 MHz, CDCl3): δ 6.75 (d, 2H, J=9.2 Hz), 6.62 (s, 1H), 6.38 (d, 2H, J=9.2 Hz),4.25-4.11 (m, 3H), 3.73 (s, 3H), 3.19 (heptet, 1H, J=7.0 Hz), 2.06 (s, 3H), 1.33 (d, 6H, J=7.0 Hz), 1.27 (s, 6H), 1.11 (br m, 6H).

Provenance & Evidence