反応 #1356
ord-c816ac4ef7654d68886954c067ebcb25
反応方程式
反応物
試薬
反応条件
後処理
- 1その他A 300-ml three-necked round flask equipped with a stirring bar
- 2workup.ADDITIONTo the mixture was gradually dropwise added a solution
- 3workup.ADDITIONAfter the addition
- 4その他was elevated to room temperature
- 5その他The organic phase was separated
- 6抽出the aqueous phase was extracted with 50 ml of methylene chloride two times
- 7洗浄The combined organic phase was washed with water
- 8乾燥by drying over anhydrous Na2SO4
- 9その他The solvent was evaporated under reduced pressure
- 10その他The residue was chromatographed on silica gel (eluting with hexane, and hexane/ethyl acetate (100/3 parts by volume))
実験手順
A 300-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a dropping funnel and a thermometer was charged with 12.3 g (36.3 mmol) of 2-ethyl-1-hydroxy-4-(9-phenanthryl)indane, 19.7 ml (142 mmol) of triethylamine and 61.5 ml of methylene chloride. To the mixture was gradually dropwise added a solution containing 3.3 ml (42.6 mmol) of methansulfonyl chloride dissolved in 5 ml of methylene chloride under a nitrogen atmosphere at 0° C. After the addition was completed, the temperature was elevated to room temperature, and the reaction mixture was stirred for additional 4 hours. To the reaction mixture was added 80 ml of a saturated aqueous solution of sodium bicarbonate. The organic phase was separated, and the aqueous phase was extracted with 50 ml of methylene chloride two times. The combined organic phase was washed with water, and then a saturated aqueous solution of sodium chloride, followed by drying over anhydrous Na2SO4. The solvent was evaporated under reduced pressure. The residue was chromatographed on silica gel (eluting with hexane, and hexane/ethyl acetate (100/3 parts by volume)) to give 9.61 g of the desired product (mixture of two isomers) as a pasty pale yellow-green liquid (yield: 83%).