Reaction Steps
2,12-Bis-(4-isobutyl-phenyl)-2,12-dimethyl-7-([1,3]dithianyl)-tridecanedioic acid diethyl ester (5.81 g, 8.33 mmol) was dissolved in freshly distilled tetrahydrofuran (THF, 50 mL) and added to lithium aluminum hydride (1.0 g, 26.3 mmol) in THF (50 mL) at −78° C. under a nitrogen atmosphere. The solution was warmed to room temperature over four hours. The reaction was then cooled back to −78° C. and quenched with ethyl acetate (5.0 mL). After warming to room temperature, water (100 mL) was added and the product was extracted with diethyl ether (2×100 mL). The ether extracts were combined, dried with sodium sulfate, filtered, and concentrated. After drying under high vacuum for four hours, the reaction yielded 2,12-bis-(4-isobutyl-phenyl)-2,12-dimethyl-7-([1,3]dithianyl)-tridecane-1,13-diol (4.80 g, 94% yield) as a colorless oil. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm) 7.20 (d, 4H, J=8.0 Hz), 7.09 (d, 4H, J=8.0 Hz), 3.64 (d, 2H, J=10.7 Hz), 3.48 (d, 2H, J=10.7 Hz), 2.71 (t, 4H, J=5.1 Hz), 2.50-2.35 (m br., 2H), 2.43 (d, 4H, J=7.0 Hz), 1.90-1.80 (m, 4H), 1.80-1.68 (m, 6H), 1.58-1.42 (m, 2H), 1.38-1.25 (m, 4H), 1.30 (s, 6H), 1.26-1.10 (m, 2H), 1.10-0.95 (m, 2H), 0.89 (d, 12H, J=6.6 Hz). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm) 141.94, 139.39, 129.20, 126.44, 72.48, 53.30, 44.97, 43.09, 38.45, 38.18, 30.21, 26.01, 25.64, 24.84, 24.09, 22.55, 21.64. HRMS (LSIMS, nba): Calcd. for C38H61O2S2 (MH+): 613.4113, found: 613.407.
