반응 #49835

반응 방정식

1-naphthoaldehyde

diethyl malonate

piperidine

→

2-(1-naphthylmethyl)-1,3-propanediol

수율 90.3%

용매

benzene

반응 조건

후처리

1. 1
   온도the solution was refluxed
2. 2
   온도under heating for 6 hours
3. 3
   기타while removing water
4. 4
   workup.DISTILLATIONby azeotropic distillation
5. 5
   workup.ADDITIONThe reaction solution was diluted with benzene
6. 6
   세척washed sequentially with 1N hydrochloric acid, with a saturated sodium hydrogencarbonate aqueous solution, with water and with a saturated sodium chloride aqueous solution
7. 7
   건조dried over anhydrous magnesium sulfate
8. 8
   workup.DISTILLATIONThen, the solvent was distilled off under reduced pressure
9. 9
   workup.DISSOLUTIONThe residue was dissolved in a mixture
10. 10
    workup.ADDITIONwere added
11. 11
    온도under cooling with ice
12. 12
    농축concentrated under reduced pressure
13. 13
    workup.ADDITIONWater was added to the residue
14. 14
    추출extracted with ethyl acetate
15. 15
    세척The extract layer was washed with a saturated sodium hydrogencarbonate aqueous solution, with water and with a saturated sodium chloride aqueous solution
16. 16
    건조dried over anhydrous magnesium sulfate
17. 17
    workup.DISTILLATIONThen, solvent was distilled off under reduced pressure
18. 18
    기타The residue was recrystallized from diethyl ether-n-hexane

실험 절차

2 g of 1-naphthoaldehyde, 2.3 g of diethyl malonate and 0.2 ml of piperidine were dissolved in 10 ml of benzene, and the solution was refluxed under heating for 6 hours while removing water by azeotropic distillation. The reaction solution was diluted with benzene, washed sequentially with 1N hydrochloric acid, with a saturated sodium hydrogencarbonate aqueous solution, with water and with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure. The residue was dissolved in a mixture consisting of 55 ml of ethanol and 37 ml of THF, and 2.7 g of sodium borohydride and 3.0 g of lithium chloride were added thereto under cooling with ice. The mixture was stirred at room temperature for 1 hour and then concentrated under reduced pressure. Water was added to the residue, and the solution was neutralized with 6N hydrochloric acid and extracted with ethyl acetate. The extract layer was washed with a saturated sodium hydrogencarbonate aqueous solution, with water and with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. Then, solvent was distilled off under reduced pressure. The residue was recrystallized from diethyl ether-n-hexane to obtain 2.5 g of 2-(1-naphthylmethyl)-1,3-propanediol.

출처