Chlorotrimethylsilane → 4-Bromo-2-i-butyl-1-trimethylsilyloxyindane

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-2-1-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%).

1. customA 300-ml three-necked round flask equipped with a stirring bar
2. temperaturewhile cooling with ice bath
3. additionAfter the addition
4. customwas elevated to room temperature
5. customThen, the organic phase was separated
6. extractionthe aqueous phase was further extracted with 50 ml of methylene chloride two times
7. washThe combined organic phase was washed with 100 ml of a saturated NaCl aq.
8. dry with materialby dried over anhydrous Na2SO4
9. customThe solvent was evaporated under reduced pressure
10. distillationThe residue was distilled under reduced pressure

ORDレコード

ord-1198b2dcde014309a3f081879ae92d45

出典データセット

uspto-grants-1997_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05658997