Реакция #1360

Уравнение реакции

sodium bicarbonate

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

triethylamine

trimethylsilyl chloride

→

desired product

Выход 96.0%

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

Выход 96.0%

Растворители

methylene chloride

methylene chloride

Условия реакции

Обработка

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

Методика

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%).

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