Short Synthetic Route to Retinoids Through Dialkylation of 3- Methyl -3-Sulfolene
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Selected spectral values: Compound 6 : IR ν max (Neat) 3413, 2930, 1625, 1445, 992, 885. cm−1 1H NMR (300 MHz, CDCl3). δ 6.25 (1H. d. J=15.70 Hz, H-12), 5.68 (1H. dd. J=15.70. 5.85 Hz H-11), 5.60 (1H. t, J=6.60 Hz. H-14), 5.33 (1H, t, J=6.40 Hz, H-8), 4.59 (1H,d, J=5.85 Hz, H-10), 4.05 (2H, d, J=6.60 Hz, H-15), 3.34 (3H, s-OCH3), 2.73 (2H, d, J=6.40 Hz, H-7), 1.93 (2H, t, J=6.2 Hz), 1.78 (3H, d, J=1.09 Hz), 1.65 (3H, d, J = 1.0 Hz), 1.6 (3H, m), 1.53 (3H, s), 1.41 (2H, m), 0.96 (6H, s). Compound 10: IR νmax (Neat) 2937, 1625, 1451, 898. cm−1. UV (Heptane): λ max:328 nm, (ε 3.66 × 10 4).1H NMR (300 MHz.CDCl3), δ 6.52 (1H,dd, J=10.60, 17.0 Hz, H-13), 6.44 (1H, d, J=11.70 Hz ,H-7), 6.40 (1H, d, J=11.70 Hz, H-8), 6.17 (2H, s, H-11 & 12), 5.24 (1H, d, J=17.0 Hz, H-14), 5.05 (1H, d, J=10.60 Hz, H-14), 2.02 (2H, t, J=6.20 Hz), 1.95 (3H, d. J=0.70 Hz), 1.90 (2H, d. J=0.73 Hz), 1.72 (3H. s), 1.62 (2H, m), 1.45 (2H, m), 1.02 (6H, s)