반응 #488994

반응 방정식

tert-butyl (2-hydroxyethyl)carbamate

Sodium hydride

3-chloro-2-(chloromethyl)prop-1-ene

AcOH

→

title compound

수율 56.0%

tert-Butyl 6-methylene-1,4-oxazepane-4-carboxylate

수율 56.0%

용매

THF

dimethylformamide

반응 조건

후처리

1. 1
   기타evaporated in a water aspirator in vacuo at 45-55° C.
2. 2
   온도reflux condenser
3. 3
   workup.ADDITIONThe residue was poured with water (300 mL)
4. 4
   추출extracted with a mixture of ethylacetate (200 mL), hexane (100 mL) and chloroform (50 mL)
5. 5
   기타The organic layer was separated
6. 6
   세척washed with water (2×100 mL) and brine
7. 7
   추출The combined aqueous layer was extracted with a mixture of ethylacetate (150 mL) and hexane (50 mL)
8. 8
   기타The organic layer was separated
9. 9
   세척washed with water (2×100 mL) and brine
10. 10
    여과The extracts were filtered sequentially through silica gel (25 g) and sodium sulphate (50 mL)
11. 11
    세척eluting with chloroform (100 mL)
12. 12
    기타The filtrate was evaporated
13. 13
    workup.DISTILLATIONthe residue was distilled in vacuo

실험 절차

60% Sodium hydride in oil (26 g, 0.65 mol, 2.17 eq) was added in one portion in a stream of argon at 5° C. to a solution of 3-chloro-2-(chloromethyl)prop-1-ene (35 mL, 0.3 mol, 1 eq) in dimethylformamide (500 mL). Then a solution of tert-butyl (2-hydroxyethyl)carbamate (48.3 g, 0.3 mol, 1 eq) in THF (500 mL) was added, and the reaction mixture was heated to 25° C. and stirred at this temperature for 2 h. The reaction mixture was then neutralized with glacial AcOH (4.5 mL) and evaporated in a water aspirator in vacuo at 45-55° C. using a 15-cm reflux condenser. The residue was poured with water (300 mL) and extracted with a mixture of ethylacetate (200 mL), hexane (100 mL) and chloroform (50 mL). The organic layer was separated and washed with water (2×100 mL) and brine. The combined aqueous layer was extracted with a mixture of ethylacetate (150 mL) and hexane (50 mL). The organic layer was separated and washed with water (2×100 mL) and brine. The extracts were filtered sequentially through silica gel (25 g) and sodium sulphate (50 mL), eluting with chloroform (100 mL). The filtrate was evaporated, and the residue was distilled in vacuo to give title compound as a colorless oil (bp 76-79° C. at 0.7 mm Hg) (35.8 g, 0.168 mol, 53%).

출처