Pyridine → HCID 11092045, compound

Participants

Reaction Steps

To a stirred mixture of 1.3 g (0.054 mole) of sodium hydride, 10.8 g (7.5 ml, 0.063 mole) of benzyl bromide and 50 ml dry tetrahydrofuran or other aprotic solvent under a dry nitrogen atmosphere were added slowly a solution of 14.8 g (0.038 mole) of crude methyl 2-deoxy-5-O-tritylribofuranoside in 100 ml of dry tetrahydrofuran. After the addition was completed (0.5 hr), the mixture was stirred at ambient temperature for 4 hrs., then at 65°-70° C. for an additional 2 hrs. The mixture was cooled, vacuum filtered through filter-aid, then heated at reflux for 2 hrs. with 15 ml (0.2 mole) of pyridine to consume the excess benzyl bromide. The mixture was again cooled and vacuum filtered through filter-aid. The solvent was removed from the filtrate under reduced pressure. Toluene (2×150 ml) was then added and evaporated. The residue (24.3 g.) was taken up in ethyl acetate (200 ml), washed with saturated NaCl solution (150 ml), then with DI water (150 ml). The organic phase was dried (Na2SO4), filtered and the solvent evaporated under vacuum. The red-orange oil that remained was used directly in subsequent coupling reactions. An analytical sample was prepared by chromatography on silica gel eluting with 10% ethyl acetate in hexane. The light-yellow oil thus prepared showed the following: 1H NMR (CDCl3) δ2.05 (m, 2, CH2), 3.18 (s, 3, OCH3), 3.33 (s, 2, CH2), 3.6 to 4.4 (m, 2, OCH), 4.42 (d, 2, CH2), 4.9 to 5.1 (m, 1, anomeric CH), 7.1 to 7.7 (m, 20, ArH); IR (neat) 3090 cm-1 (w), 3060 (m), 3035 (m), 2920 (m), 1598 (w), 1490 (m), 1448 (s), 1362 (m), 1080 (s), 762 (m), 748 (m), 705 (s), 633 (m).

Provenance & Evidence