反应详情

To a solution of NaH (2.4 g, 99 mmol) in 100 mL of DMF cooled to 0° C. is added benzylmercaptan (12.3 g, 99 mmol). The solution was allowed to warm to room temperature then recooled to 0° C. 2-Fluoro-3-methylpyridine in 10 mL DMF was added dropwise and stirred at room temperature overnight. The solution was diluted with H2O, extracted twice with Et2O, twice with EtOAc, and the combined organics washed twice with saturated NaHCO3, dried and concentrated. The resulting oil was flash chromatographed (10% Et2O/hexane (v/v)) to yield 16.3 g of the desired product. NMR (200 MHz, CDCl3) δ 2.24 (s, 3H), 4.50 (s, 2H), 6.9 (dd, 1H), 7.2 (m, 5H), 7.4 (d, 1H) and 8.3 (d, 1H).

1. customthen recooled to 0° C
2. extractionextracted twice with Et2O, twice with EtOAc
3. washthe combined organics washed twice with saturated NaHCO3
4. customdried
5. concentrationconcentrated
6. customchromatographed (10% Et2O/hexane (v/v))