반응 #79501

반응 방정식

sodium hydrogencarbonate

1-(1H-imidazol-4-yl)-2-methyl-1-propanone

2-bromo-6-methoxynaphthalene

magnesium

→

1-(1H-imidazol-4-yl)-1-(6-methoxynaphthalen-2-yl)-2-methylpropanol

수율 84.0%

용매

water

THF

THF

THF

반응 조건

후처리

1. 1
   기타higher than 50° C.
2. 2
   workup.STIRRINGthe mixture was stirred at 15 to 25° C. for 1.5 h
3. 3
   workup.STIRRINGthe mixture was stirred at 15 to 25° C. for 8 h
4. 4
   workup.STIRRINGAfter stirring
5. 5
   기타After partitioning
6. 6
   추출the aqueous layer was extracted with ethyl acetate (5 ml)
7. 7
   세척the mixture was washed with saturated brine
8. 8
   농축concentrated under reduced pressure
9. 9
   여과the crystals were collected by filtration
10. 10
    세척washed with isopropyl ether (12 ml)
11. 11
    기타The crystals were dried in vacuo (40° C.)

실험 절차

THF (14 ml) was added to magnesium (0.55 g, 22.4 mmol) under a nitrogen atmosphere. Iodine (3 mg) was added and the mixture was stirred. While keeping the mixture at not higher than 50° C., a solution of 2-bromo-6-methoxynaphthalene (5.15 g, 21.7 mmol.) in THF (12 ml) was added dropwise, and the mixture was stirred at 15 to 25° C. for 1.5 h. A solution of 1-(1H-imidazol-4-yl)-2-methyl-1-propanone (1 g, 7.24 mmol) in THF (5 ml) was added dropwise at −20° C., and the mixture was stirred at 15 to 25° C. for 8 h. A saturated aqueous sodium hydrogencarbonate (5 ml) and water (5 ml) were successively added dropwise. After stirring, the mixture was passed through celite. After partitioning, the aqueous layer was extracted with ethyl acetate (5 ml). The organic layer was combined, and the mixture was washed with saturated brine and concentrated under reduced pressure. The concentration residue was broken up with ethyl acetate (6 ml) and isopropyl ether (12 ml), and the crystals were collected by filtration and washed with isopropyl ether (12 ml). The crystals were dried in vacuo (40° C.) to give 1-(1H-imidazol-4-yl)-1-(6-methoxynaphthalen-2-yl)-2-methylpropanol (1.8 g, yield 84%).

출처