تفاعل #65976

معادلة التفاعل

2-bromomethylnaphthalene

indanone

K2CO3

18-crown-6

→

title compound

6-[(2-Naphthyl)methoxy]-2-methyl-indanone

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

1. 1
   أخرىprepared
2. 2
   أخرىThe acetonitrile is evaporated
3. 3
   workup.DISSOLUTIONthe residue is dissolved in water
4. 4
   استخلاصextracted with ethyl acetate
5. 5
   تجفيفdried (MgSO4)
6. 6
   أخرىevaporated to dryness
7. 7
   أخرىchromatographed
8. 8
   أخرى(on silica Merck-60, preabsorbed in CH2Cl2, eluted with 8:2 hexane-ethyl acetate)

الإجراء التجريبي

A mixture of the indanone (14 g, 86.4 mmole) prepared as described in Example 1, Step D, anhydrous K2CO3 (11.24 g, 81.4 mmole), 18-crown-6 (2.29 g, 6.4 mmole) and 2-bromomethylnaphthalene (11.6 g, 95 mmole) in acetonitrile (275 mL) is heated under nitrogen for 24 hours (in an oil bath set at 70° C.). The acetonitrile is evaporated and the residue is dissolved in water, extracted with ethyl acetate, dried (MgSO4) and evaporated to dryness. The crude product (tan solid) is flash chromatographed (on silica Merck-60, preabsorbed in CH2Cl2, eluted with 8:2 hexane-ethyl acetate) to provide the title compound as a white solid (13.49 g, 52% ).

المصدر