反应详情

Sodium hydride (80% dispersion in oil, 1.68 g) was added portionwise to a solution of 2-pyridineethanol (6.88 g) in 1,2-dimethoxyethane (50 ml) and stirred under nitrogen for 18 h at room temperature. A solution of 2-(phenylmethoxy)ethanol methanesulphonate (8.25 g) in 1,2-dimethoxyethane (100 ml) was added and the mixture stirred at room temperature for 7 h, then poured into water (400 ml) and extracted with diethyl ether (3×200 ml). The ethereal extracts were washed with 2N hydrochloric acid (250 ml). The aqueous phase was re-extracted with diethyl ether (100 ml) and the aqueous phase carefully basified with 8% sodium bicarbonate to pH8. Extraction with diethyl ether (2×200 ml) and drying and evaporation in vacuo of the organic extracts gave an oil. Purification by FCC eluting with System F (4.1→1.1) gave the title compound (2.71 g) as an oil. T.l.c. (diethyl ether) Rf 0.54

1. stirringthe mixture stirred at room temperature for 7 h
2. extractionextracted with diethyl ether (3×200 ml)
3. washThe ethereal extracts were washed with 2N hydrochloric acid (250 ml)
4. extractionThe aqueous phase was re-extracted with diethyl ether (100 ml)
5. extractionExtraction with diethyl ether (2×200 ml)
6. customdrying
7. customevaporation in vacuo of the organic extracts
8. customgave an oil
9. customPurification by FCC
10. washeluting with System F (4.1→1.1)