反应详情

A solution of tert-butyl 2-hydroxyethylcarbamate 38.1 (9.00 mL, 58.2 mmol) in DMF (50.0 mL) was cooled in a ice bath and treated portion wise with sodium hydride (60% in mineral, 5.12 g, 128 mmol). The mixture was stirred in ice bath for 15 minutes and then treated with 3-chloro-2-(chloromethyl)prop-1-ene (7.07 mL, 61.1 mmol). After addition was complete, the ice bath was removed and the reaction mixture was stirred was stirred at room temperature overnight. The mixture was diluted with water and extracted with ether. The combined organics were dried over Na2SO4, filtered and concentrated in vacuo to afford an oil which purified by flash chromatography (gradient EtAOAc/hexane 5%-40%) to afford the desired product (4.6, 37% yield) clear oil. LCMS 114.10 [M-tBuCO2]+.

1. additionAfter addition
2. customthe ice bath was removed
3. stirringthe reaction mixture was stirred
4. stirringwas stirred at room temperature overnight
5. additionThe mixture was diluted with water
6. extractionextracted with ether
7. dry with materialThe combined organics were dried over Na2SO4
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto afford an oil which
11. custompurified by flash chromatography (gradient EtAOAc/hexane 5%-40%)