Réaction #1360

Équation de réaction

sodium bicarbonate

4-bromo-2-i-butyl-1-hydoxyindane

triethylamine

trimethylsilyl chloride

→

desired product

Rendement 96.0%

4-bromo-2-i-butyl-1-trimethylsilyloxyindane

Rendement 96.0%

Solvants

methylene chloride

methylene chloride

Conditions de réaction

Traitement

1. 1
   AutreA 300-ml three-necked round flask equipped with a stirring bar
2. 2
   Températurewhile cooling with ice bath
3. 3
   workup.ADDITIONAfter the addition
4. 4
   Autrewas elevated to room temperature
5. 5
   AutreThen, the organic phase was separated
6. 6
   Extractionthe aqueous phase was further extracted with 50 ml of methylene chloride two times
7. 7
   LavageThe combined organic phase was washed with 100 ml of a saturated NaCl aq.
8. 8
   Séchageby dried over anhydrous Na2SO4
9. 9
   AutreThe solvent was evaporated under reduced pressure
10. 10
    workup.DISTILLATIONThe residue was distilled under reduced pressure

Mode opératoire

A 300-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a dropping funnel and a thermometer was charged with 34.4 g (127.8 mmol) of 4-bromo-2-i-butyl-1-hydoxyindane, 23.1 ml (166.2 mmol) of triethylamine and 118 ml of methylene chloride. To the mixture was added dropwise 20 ml of a methylene chloride solution containing 19.45 ml (153.4 mmol) of trimethylsilyl chloride under a nitrogen atmosphere while cooling with ice bath. After the addition was completed, the temperature was elevated to room temperature, and the mixture was further stirred for 1.5 hours. The reaction mixture was poured onto a mixture of 200 ml of ice water and 20 ml of a saturated aqueous solution of sodium bicarbonate. Then, the organic phase was separated, and the aqueous phase was further extracted with 50 ml of methylene chloride two times. The combined organic phase was washed with 100 ml of a saturated NaCl aq., followed by dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure. The residue was distilled under reduced pressure to obtain 41.8 g of the desired product (mixture of two isomers) as a pale yellow liquid (yield: 96%).

Source