반응 #1880957

반응 방정식

methyl 4-allyl-2-(ethoxycarbonylmethoxy)phenoxyacetate

sodium hydride

hydrochloric acid

→

7-allylbenzo[b][1,4]dioxepin-3-one

수율 42.0%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   온도The reaction mixture was then refluxed for 20 h
2. 2
   온도after cooling
3. 3
   추출extracted three times
4. 4
   건조The combined ether extracts were dried over sodium sulfate
5. 5
   기타freed from solvent on a rotary evaporator
6. 6
   workup.ADDITION400 ml of 2N hydrochloric acid were added
7. 7
   온도the mixture was refluxed for 20 h
8. 8
   workup.ADDITIONThe mixture was then poured into 1.5 l of ice water
9. 9
   추출the product was extracted four times
10. 10
    세척each time with 1.5 l of ether, and the combined ether extracts were washed with 1 l of water and 100 ml of saturated sodium chloride solution
11. 11
    건조After drying over sodium sulfate, concentration on a rotary evaporator and flash chromatography

실험 절차

A solution of 69.0 g (234 mmol) of methyl 4-allyl-2-(ethoxycarbonylmethoxy)phenoxyacetate was added dropwise in the course of 2.5 h to a suspension of 12.0 g (500 mmol) of sodium hydride in 500 ml of tetrahydrofuran. The reaction mixture was then refluxed for 20 h and, after cooling, poured into 1.5 l of ice water. The resultant mixture was acidified to pH 2 with 2N hydrochloric acid and extracted three times, each time with 2 l of ether. The combined ether extracts were dried over sodium sulfate, freed from solvent on a rotary evaporator and taken up into 400 ml of ethanol. 400 ml of 2N hydrochloric acid were added and the mixture was refluxed for 20 h. The mixture was then poured into 1.5 l of ice water, the product was extracted four times, each time with 1.5 l of ether, and the combined ether extracts were washed with 1 l of water and 100 ml of saturated sodium chloride solution. After drying over sodium sulfate, concentration on a rotary evaporator and flash chromatography. (pentane/ether, 4:1, Rf=0.37) on silica gel, 20.0 g (42%) of 7-allylbenzo[b][1,4]dioxepin-3-one (1) were obtained as a colorless liquid.

출처