反応 #90094

反応方程式

1-bromo-2-(2-bromo-ethoxy)-ethane

7-methoxy-3,4-dihydro-1H-naphthalen-2-one

7-Methoxy-3,4-dihydro-1H-naphthalen-2-one

Compound A1

7-Methoxy-3,4-dihydro-1H-naphthalen-2-one

sodium hydride

ammonium chloride

→

title compound

収率 51.0%

7-Methoxy-2′,3,3′,4,5′,6′-hexahydro-2H-spiro[naphthalene-1,4′-pyran]-2-one

収率 51.0%

溶媒

THF

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred at 80° C. for 3 hr
2. 2
   抽出the extraction
3. 3
   乾燥The organic layer was dried over magnesium sulfate
4. 4
   その他The drying agent was removed by filtration
5. 5
   その他the residues obtained
6. 6
   濃縮after concentration under reduced pressure
7. 7
   その他were purified by silica gel column chromatography (ethyl acetate/hexane)

実験手順

To the THF (300 ml) solution of 7-methoxy-3,4-dihydro-1H-naphthalen-2-one (Compound A1, 20 g, 0.11 mol), sodium hydride (9.9 g, 3.7 eq.) was added at 0° C. After stirring for 10 min, 1-bromo-2-(2-bromo-ethoxy)-ethane (19 ml, 12 eq.) was added dropwise thereto, and the mixture was stirred at 80° C. for 3 hr. To the reaction solution, saturated aqueous solution of ammonium chloride was added and the extraction was carried out twice with ethyl acetate. The organic layer was dried over magnesium sulfate. The drying agent was removed by filtration and the residues obtained after concentration under reduced pressure were purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (white solid, 13 g, 51%).

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