Pyridine → HCID 67789353, compound

Participants

Reaction Steps

0.06 ml of pyridine and 0.1 ml of triethylchlorosilane were added successively at 0° C. to 100 mg (0.39 mmol) of the hydroxyethyl compound from step 1 in 3 ml of anhydrous methylene chloride and then stirred at room temperature for 3 h. The reaction mixture was diluted with 10 ml of methylene chloride and washed successively with dilute hydrochloric acid, saturated NaHCO3 solution and water. After drying over sodium sulfate and concentration in vacuo, the residue was chromatographed on silica gel (eluent: toluene/ethyl acetate=1:2). Yield: 122 mg (85%). -1H-NMR (200 MHz, CDCl3): δ=0.50-0.70 (2×m, 6H and 9H, SiCH3CH3); 1.28 (d, 3H, CH--CH3); 1.95-2.38 (m, 2H, CH--CH2 --CH2); 2.76 (dt, 1H, CH--CH2 --CH2) 3.02-3.16 (m, 3H, CH--CH2 --CH2 and H-3); 4.23 (mc, 1H, CH--CH3); 4.43 (dd, 1H, H-4); 5.8 (bs, 1H, NH); 7.22-7.38 and 7.45-7.57 (2×m, 3 H, aromatic H); 8.02 (dd, 1H, aromatic H).

Provenance & Evidence