تفاعل #62227

معادلة التفاعل

34

5-isopropoxy-6-methoxy-1,2,3,4-tetrahydronaphtalene

water dioxane

→

35

المردود 71.0%

5-Isopropoxy-6-methoxy-3,4-dihydro-2H-naphthalen-1-one

المردود 71.0%

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added dropwise to the reaction mixture
2. 2
   أخرىThe solid separated
3. 3
   ترشيحwas filtered
4. 4
   غسيلwashed with ethylacetate
5. 5
   تركيزThe filtrate was concentrated under reduced pressure and 10 mL of saturated sodium bicarbonate solution
6. 6
   workup.ADDITIONwas added
7. 7
   أخرىthe resulting reaction mixture
8. 8
   استخلاصwas extracted with ether (3×20 mL)
9. 9
   تجفيفthe combined organic phases dried over anhydrous sodium sulfate
10. 10
    ترشيحfiltered
11. 11
    أخرىevaporated in vacuo
12. 12
    أخرىPurification by flash column chromatography (silica gel, 30:70 EtOAc:Hexanes)

الإجراء التجريبي

34 (120 mg, 0.55 mmol) was weighed in a 100 mL round bottom flask and a solution of 5 mL of water:dioxane (5:95) was added and the reaction was set up under nitrogen. A solution of 2,4-dichloro-5,6-dicyanobenzoquinone (0.25 g, 1.09 mmol) dissolved in 5 mL of dioxane was added dropwise to the reaction mixture. The reaction mixture was stirred for 12 h. The solid separated was filtered and washed with ethylacetate. The filtrate was concentrated under reduced pressure and 10 mL of saturated sodium bicarbonate solution was added and the resulting reaction mixture was extracted with ether (3×20 mL) and the combined organic phases dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. Purification by flash column chromatography (silica gel, 30:70 EtOAc:Hexanes) yielded 90 mg (71%) of 35. Rf value: 0.458 (40:60 EtOAc:Hexanes).

المصدر