تفاعل #955978

معادلة التفاعل

ethyl acetate hexane

NaH

1-tetralone

EtOAc Hexane

methyl iodide

→

2,2-dimethyl-1-tetralone

المردود 83.0%

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

المردود 83.0%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added
2. 2
   درجة الحرارةThe mixture was heated on an oil bath to 40° C. for 30 minutes
3. 3
   workup.STIRRINGstirring
4. 4
   أخرىcontinued at RT until the starting material
5. 5
   أخرىThe reaction was quenched by addition of water (slowly and dropwise)
6. 6
   أخرىto destroy excess sodium hydride
7. 7
   استخلاصThe mixture was extracted with ethyl acetate
8. 8
   غسيلwashed with water
9. 9
   تجفيفdried over sodium sulphate
10. 10
    أخرىEvaporation of the solvent
11. 11
    أخرىyielded a brown oil

الإجراء التجريبي

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%).

المصدر