반응 #69514

반응 방정식

ammonium chloride

allyl benzyl ether

trichloroacetyl chloride

sodium hydrogencarbonate

→

title compound

수율 50.5%

3-[(Benzyloxy)methyl]cyclobutanone

수율 50.5%

용매

n-heptane ethyl acetate

diethyl ether

dimethoxyethane

반응 조건

후처리

1. 1
   workup.STIRRINGthe mixture was stirred at mom temperature for six hours
2. 2
   workup.ADDITIONThe reaction mixture was poured into ice-
3. 3
   추출extracted with ethyl acetate
4. 4
   건조dried over anhydrous magnesium sulfate
5. 5
   여과The mixture was filtered
6. 6
   workup.DISTILLATIONthe solvent in the filtrate was distilled off under reduced pressure
7. 7
   기타The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate
8. 8
   workup.DISSOLUTIONThe obtained dichloro product was dissolved in methanol (200 mL)
9. 9
   workup.STIRRINGwhile vigorously stirring
10. 10
    여과the insoluble matters were filtered off with Celite
11. 11
    workup.DISTILLATIONthe filtrate was distilled off under reduced pressure
12. 12
    workup.ADDITIONWater was added to the residue, which
13. 13
    추출was extracted with ethyl acetate
14. 14
    건조dried over anhydrous magnesium sulfate
15. 15
    여과The mixture was filtered
16. 16
    workup.DISTILLATIONthe solvent in the filtrate was then distilled off under reduced pressure
17. 17
    기타The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate

실험 절차

To a diethyl ether (100 mL) solution of allyl benzyl ether (11.1 g, 75.0 mmol), was added zinc copper couple (74.5 g, 33.0 mmol) while stirring at room temperature, a dimethoxyethane (100 mL) solution of trichloroacetyl chloride (43.6 mL, 375 mmol) was added dropwise, and the mixture was stirred at mom temperature for six hours. The reaction mixture was poured into ice-cooled aqueous sodium hydrogencarbonate (500 mL), extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The mixture was filtered and then the solvent in the filtrate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=15/1). The obtained dichloro product was dissolved in methanol (200 mL), ammonium chloride (20.0 g, 375 mmol) was added and zinc powder (30.0 g, 450 mmol) was added little by little while vigorously stirring. After the reaction was completed, the insoluble matters were filtered off with Celite, the filtrate was distilled off under reduced pressure. Water was added to the residue, which was extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The mixture was filtered, and the solvent in the filtrate was then distilled off under reduced pressure. The residue was purified by silica gel column chromatography (a mixed solvent of n-heptane and ethyl acetate: n-heptane/ethyl acetate=15/1 then 12/1) to obtain the title compound (7.20 g, 37.9 mmol).

출처