Реакция #49835

Уравнение реакции

1-naphthoaldehyde

diethyl malonate

piperidine

→

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

Выход 90.3%

Растворители

benzene

Условия реакции

Обработка

1. 1
   Температураthe solution was refluxed
2. 2
   Температураunder heating for 6 hours
3. 3
   Другоеwhile removing water
4. 4
   workup.DISTILLATIONby azeotropic distillation
5. 5
   workup.ADDITIONThe reaction solution was diluted with benzene
6. 6
   Промывкаwashed sequentially with 1N hydrochloric acid, with a saturated sodium hydrogencarbonate aqueous solution, with water and with a saturated sodium chloride aqueous solution
7. 7
   Сушкаdried 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
    Температураunder cooling with ice
12. 12
    Концентрированиеconcentrated under reduced pressure
13. 13
    workup.ADDITIONWater was added to the residue
14. 14
    Экстракцияextracted with ethyl acetate
15. 15
    ПромывкаThe extract layer was washed with a saturated sodium hydrogencarbonate aqueous solution, with water and with a saturated sodium chloride aqueous solution
16. 16
    Сушкаdried over anhydrous magnesium sulfate
17. 17
    workup.DISTILLATIONThen, solvent was distilled off under reduced pressure
18. 18
    ДругоеThe residue was recrystallized from diethyl ether-n-hexane

Методика

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.

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