Reacción #65907

Ecuación de reacción

magnesium

title product

2,4-bis(1,1-dimethylethyl)-1-bromobenzene

Ethylene oxide

→

title compound

2,4-bis(1,1-dimethylethyl)benzeneethanol

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONAfter the addition
2. 2
   Temperaturathe mixture is refluxed for one hour
3. 3
   Temperaturarefluxing
4. 4
   Otropartitioned between saturated ammonium chloride and diethyl ether
5. 5
   ExtracciónThe aqueous layer is further extracted with ether
6. 6
   Lavadothe combined organic extracts washed with brine
7. 7
   Secadodried over sodium sulfate
8. 8
   Filtraciónfiltered
9. 9
   Otroevaporated

Procedimiento

To 243 mg (10 mmoles) of magnesium turnings in 10 ml of tetrahydrofuran is added dropwise a solution of 2.69 grams (10 mmoles) of the title product of Example 9 in 5 ml of tetrahydrofuran. After the addition is complete, the mixture is refluxed for one hour. Ethylene oxide (440 mg, 10 mmoles) is then added, and refluxing continued for one hour. The mixture is cooled to room temperature and partitioned between saturated ammonium chloride and diethyl ether. The aqueous layer is further extracted with ether, the combined organic extracts washed with brine, dried over sodium sulfate, filtered, and evaporated. Chromatography of the residue over silica gel using mixtures of ethyl acetate and hexane as eluents gives the title compound.

Fuente