반응 #1360

반응 방정식

sodium bicarbonate

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

triethylamine

trimethylsilyl chloride

→

desired product

수율 96.0%

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

수율 96.0%

용매

methylene chloride

methylene chloride

반응 조건

후처리

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

실험 절차

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%).

출처