Compound 10cH2

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Compound data: 1H NMR

Compound data: 13C NMR

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

Following the procedure for 10a, dione 14 (0.130 g, 0.292 mmol, 1 equiv.) and 1-bromo-4-tert-butylbenzene (0.40 ml, 2.336 mmol, 8 equiv.) were reacted to yield the crude diol. Diol (0.025 g, 0.035 mmol, 1 equiv.) and SnCl₂ (30 mg, 0.140 mmol, 4 equiv) were reacted at 70 °C. After 4 hours, the mixture was poured over a silica plug and washed with hexanes. Switching to 4:1 hexanes/CH₂Cl₂ eluted the product. The dihydro product was further purified using flash column chromatography using 7:3 hexanes/CH₂Cl₂ as eluent to furnish 10cH₂ as a tan solid (121 mg, 61% from 14); ¹H NMR (500 MHz, CD₂Cl₂, 25 °C) δ (ppm) 7.89 (d, J = 7.8 Hz, 2H), 7.83 (s, 2H), 7.72 (s, 2H), 7.43 (d, J = 7.4 Hz, 2H), 7.32 (d, J = 8.3 Hz, 4H), 7.29–7.21 (m, 4H), 7.13 (d, J = 8.4 Hz, 4H), 5.22 (s, 2H), 1.28 (s, 18H); ¹³C NMR (151 MHz, CD₂Cl₂, 25 °C) δ (ppm) 150.45, 150.29, 146.79, 144.85, 143.27, 137.31, 136.84, 135.09, 132.76, 127.99, 126.17, 125.07, 124.73, 124.27, 124.12, 122.29, 118.01, 51.20, 34.77, 31.48; HRMS (ES⁺) (m/z) calculated for C₄₈H₄₀S₂ (M+H)⁺ 680.2572, found 680.2539.