The sodium periodate is prepared in situ with equimolecular quantity of soda NaOH (0.5g; 12.50 mmol) and periodic acid H
5IO
6 (2.85g; 12.50 mmol), the mixture is stirred at 0°C. After 15 min, 5 ml of CCl
4, 5 ml of H
3CCN and 93.03mg (0.12mmol) of ruthenium trichloride
1,2 were added. The mixture was stirred during 15min, and then 1.85g (3.12 mmol) of
13 was added. The reaction was left under stirring at 25°C for 30h, then 20 ml of distilled water was added and the reactional mixture was extracted with the dichloromethane. After filtration on silica gel column to eliminate RuO
4, the organic layer was recovered, dried by Na
2SO
4 and evaporated under reduce pressure. The residue was purified on silica gel column using hexane: ethyl acetate (96: 4) as eluent to give 1.30g (2.18 mmol) of
2 in 70 % yield.
Melting point: 115-116 °C (Hexane)
MS (EI, 70eV): 596 (M+.).
1H NMR (300 MHz, CDCl3) d(ppm): 4.22 (1H-3, dd, J1 = 12 Hz, J2 = 4 Hz ); 7.96 (2H-2’, d, J = 8.8Hz); 7.35 (2H-3’, d, J = 8.8 Hz); 2.48 (3H-5’); 0.76 (3H-18, s); 0.85 (3H-19, s); 0.93 (3H-21, d, J = 6 Hz); 2.60 (2H-23, m); 1.10 (3H-26, d: J = 2 Hz); 1.11 (3H-27, d, J = 2 Hz); 0.80 (3H-28, s); 0.95 (3H-29, s); 1.05 (3H-30, s).
13C NMR (75 MHz, CDCl3)d (ppm): 35.15 (C-1); 27.52 (C-2); 91.00 (C-3); 36.25 (C-4); 49.98 (C-5); 38.78 (C-6); 28.03 (C-7); 133.66 (C-8); 134.93 (C-9); 36.25 (C-10); 20.20 (C-11); 25.47 (C-12); 44.16 (C-13); 50.16 (C-14); 30.76 (C-15); 30.21 (C-16); 51.33 (C-17); 18.64 (C-18); 18.99 (C-19); 37.01 (C-20); 21.54 (C-21); 37.59 (C-22); 29.84 (C-23); 215.50 (C-24); 35.64 (C-25); 21.72 (C-26); 22.40 (C-27); 31.80 (C-25); 21.70 (C-26); 18.80 (C-27); 14.5 (C-28); 16.41 (C-29); 144.35 (C-1’); 129.76 (C-2’); 127.77 (C-3’); 134.82 (C-4’); 21.25 (C-5’).
MS (m/z): 596 (35%), 425 (48%), 297 (75%).