Reacción #955978

Ecuación de reacción

ethyl acetate hexane

NaH

1-tetralone

EtOAc Hexane

methyl iodide

→

2,2-dimethyl-1-tetralone

Rendimiento 83.0%

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

Rendimiento 83.0%

Disolventes

THF

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   TemperaturaThe mixture was heated on an oil bath to 40° C. for 30 minutes
3. 3
   workup.STIRRINGstirring
4. 4
   Otrocontinued at RT until the starting material
5. 5
   OtroThe reaction was quenched by addition of water (slowly and dropwise)
6. 6
   Otroto destroy excess sodium hydride
7. 7
   ExtracciónThe mixture was extracted with ethyl acetate
8. 8
   Lavadowashed with water
9. 9
   Secadodried over sodium sulphate
10. 10
    OtroEvaporation of the solvent
11. 11
    Otroyielded a brown oil

Procedimiento

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%).

Fuente