반응 #1929094

반응 방정식

3,4-Dihydro-2H-pyran

51

4-Bromo-1-butanol

→

product 52

수율 92.3%

2-(4-Bromobutoxy)-tetrahydro-2H-pyran

수율 92.3%

용매

dichloromethane

반응 조건

후처리

1. 1
   기타After removing the solvent
2. 2
   기타the residue was purified by flash chromatography on silica gel with 5:1 hexanes/ethyl acetate as the eluent

실험 절차

3,4-Dihydro-2H-pyran (8.5 mL, 90.96 mmol) was added dropwise to the dichloromethane (20 mL) solution of 51 (10.7 g, 69.93 mmol) and p-toluenesulfonic acid monohydrate (26.5 mg, 0.1372 mmol). The mixture was stirred at room temperature over night. After removing the solvent, the residue was purified by flash chromatography on silica gel with 5:1 hexanes/ethyl acetate as the eluent to yield product 52 as a colorless oil (15.3 g, 92%). 1H NMR (400 MHz, CDCl3): δ 1.48-1.62 (m, 4H), 1.68-1.85 (m, 4H), 1.94-2.02 (m, 2H), 3.40-3.53 (m, 4H), 3.74-3.88 (m, 2H), 4.57-4.59 (m, 1H).

출처