Isopropyl iodide → 7-t-Butyl-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-t-butyl-5-[(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran (Compound 53, 0.13 g, 0.38 mmol), 1.6M solution of n-butyllithium in hexanes (0.5 mL, 0.8 mmol) and 2-iodopropane (0.5 mL, 5 mmol) in 2 mL of anhydrous tetrahydrofuran, the title compound (0.013 g, 8.9%) was obtained as a brown oil after separation from recovered 7-t-butyl-5-[(4-methoxy-phenyl)-amino]-3,3,6-trimethyl-2,3-dihydro-benzofuran (Compound 53, 0.07 g) by preparative normal phase HPLC using 4% ethyl acetate in hexanes as the mobile phase. 1H NMR (300 MHz, C6D6): δ 6.82 (d, 2H, J=9.1 Hz), 6.75 (s, 1H), 6.56 (d, 2H, J=9.1 Hz), 4.09(heptet, 1H, J=6.5 Hz), 3.89 (s, 2H), 3.40(s, 3H), 2.40 (s, 3H), 1.68 (s, 9H), 1.10-1.25(m, 3H), 0.99-1.10(m, 3H), 0.99 (s, 6H).

Provenance & Evidence