반응 #955978

반응 방정식

ethyl acetate hexane

NaH

1-tetralone

EtOAc Hexane

methyl iodide

→

2,2-dimethyl-1-tetralone

수율 83.0%

2,2-Dimethyl-3,4-dihydro-2H-naphthalen-1-one

수율 83.0%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   온도The mixture was heated on an oil bath to 40° C. for 30 minutes
3. 3
   workup.STIRRINGstirring
4. 4
   기타continued at RT until the starting material
5. 5
   기타The reaction was quenched by addition of water (slowly and dropwise)
6. 6
   기타to destroy excess sodium hydride
7. 7
   추출The mixture was extracted with ethyl acetate
8. 8
   세척washed with water
9. 9
   건조dried over sodium sulphate
10. 10
    기타Evaporation of the solvent
11. 11
    기타yielded a brown oil

실험 절차

To a suspension of NaH (8.2 gm, 343 mmol) in THF (250 mL) in a one-liter round bottomed flask, 1-tetralone [11] (10.0 gm, 69 mmol) dissolved in dry THF (25 mL) was added. After stirring the mixture for 10 minutes at RT, methyl iodide (11.1 ml, 178 mmol) was added via a syringe. The mixture was heated on an oil bath to 40° C. for 30 minutes, and stirring continued at RT until the starting material disappeared. The reaction was monitored by TLC using ethyl acetate:hexane (1:6) solvent mixture. The reaction was quenched by addition of water (slowly and dropwise) to destroy excess sodium hydride. The mixture was extracted with ethyl acetate, washed with water and dried over sodium sulphate. Evaporation of the solvent yielded a brown oil. Column chromatography using silica gel with EtOAc:Hexane (1:6) afforded clean 2,2-dimethyl-1-tetralone [12](10.8 g, 83%).

출처