反応 #1361
ord-fb06eeebdaf54faba40d9313cc436031
反応方程式
反応条件
後処理
- 1その他A 200-ml three-necked round flask equipped with a stirring bar
- 2workup.ADDITIONTo the mixture was added dropwise a solution
- 3温度while cooling with ice bath
- 4workup.ADDITIONAfter the addition
- 5その他was elevated to room temperature
- 6その他Thereafter, the organic phase was separated
- 7抽出the aqueous phase was extracted with 50 ml of methylene chloride
- 8洗浄washed with a saturated NaCl aq.
- 9乾燥by dried over anhydrous Na2SO4
- 10その他The solvent was evaporated under reduced pressure
- 11その他The residue was separated
- 12その他purified with silica gel chromatography (eluting with hexane/ethyl acetate (20/1 parts by volume))
実験手順
A 200-ml three-necked round flask equipped with a stirring bar, a Dimroth condenser, a dropping funnel and a thermometer was charged with 4.54 g (14.4 mmol) of 2-i-butyl-1-hydroxy-4-(1-naphthyl)indene, 5.13 g (50.8 mmol) of triethylamine, 0.10 g (0.82 mmol) of 4-dimethylaminopyridine and 57.7 ml of methylene chloride. To the mixture was added dropwise a solution containing 3.87 ml (33.8 mmol) of methanesulfonyl chloride dissolved in 7.7 ml of methylene 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 3 hours. The reaction mixture was poured onto 100 ml of water. Thereafter, the organic phase was separated, and the aqueous phase was extracted with 50 ml of methylene chloride. The extracted organic phases were combined and washed with a saturated NaCl aq., followed by dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure. The residue was separated and purified with silica gel chromatography (eluting with hexane/ethyl acetate (20/1 parts by volume)) to obtain 3.98 g of the desired product (mixture of two isomers) as a pale yellow pasty liquid (yield: 93%).