반응 #2037291

반응 방정식

bromine

6-benzyloxy-3,4-dihydro-2H-naphthalen-1-one

→

title compound

7-Benzyloxy-3-bromo-1,2-dihydronaphthalene

6-benzyloxy-2-bromo-1,2,3,4-tetrahydronaphthalen-1-ol

용매

diethyl ether

반응 조건

후처리

1. 1
   추출extracted with diethyl ether
2. 2
   세척sequentially washed with a saturated aqueous solution of sodium bicarbonate, water and brine
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   여과filtered through NH silica gel
5. 5
   기타the solvent was evaporated in vacuo
6. 6
   workup.ADDITIONTo the resulting 6-benzyloxy-2-bromo-3,4-dihydro-2H-naphthalen-1-one (250 g) was added ethanol (2.5 l)
7. 7
   workup.STIRRINGthe solution was stirred
8. 8
   workup.ADDITIONsodium borohydride (25 g) was added
9. 9
   기타on an ice bath followed
10. 10
    workup.STIRRINGby stirring overnight at room temperature
11. 11
    workup.ADDITIONThe reaction mixture was poured into ice water
12. 12
    세척the resulting solid was washed with water

실험 절차

The title compound was synthesized by referring to J. Org. Chem., 1984, 49 (22), 4226. To a suspension of 6-benzyloxy-3,4-dihydro-2H-naphthalen-1-one (200 g) in diethyl ether (2 l) was added dropwise bromine (60 ml) on an ice bath, and the solution was stirred overnight at room temperature. The reaction mixture was poured into ice water, extracted with diethyl ether, then sequentially washed with a saturated aqueous solution of sodium bicarbonate, water and brine, dried over anhydrous magnesium sulfate, then filtered through NH silica gel, the solvent was evaporated in vacuo. To the resulting 6-benzyloxy-2-bromo-3,4-dihydro-2H-naphthalen-1-one (250 g) was added ethanol (2.5 l), the solution was stirred, sodium borohydride (25 g) was added thereto on an ice bath followed by stirring overnight at room temperature. The reaction mixture was poured into ice water, and the resulting solid was washed with water to provide 6-benzyloxy-2-bromo-1,2,3,4-tetrahydronaphthalen-1-ol (290 g). To a suspension of this compound (260 g) in toluene (800 ml) was added p-toluenesulfonic acid monohydrate (6.0 g), and the solution was refluxed for 2 hours. The reaction mixture was poured into ice water, extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, then filtered through NH silica gel, and the solvent was evaporated in vacuo. The residue was purified by NH silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (34 g).

출처