반응 #1361
ord-fb06eeebdaf54faba40d9313cc436031
반응 방정식
반응 조건
후처리
- 1기타A 200-ml three-necked round flask equipped with a stirring bar
- 2workup.ADDITIONTo the mixture was added dropwise a solution
- 3온도while cooling with ice bath
- 4workup.ADDITIONAfter the addition
- 5기타was elevated to room temperature
- 6기타Thereafter, the organic phase was separated
- 7추출the aqueous phase was extracted with 50 ml of methylene chloride
- 8세척washed with a saturated NaCl aq.
- 9건조by dried over anhydrous Na2SO4
- 10기타The solvent was evaporated under reduced pressure
- 11기타The residue was separated
- 12기타purified with silica gel chromatography (eluting with hexane/ethyl acetate (20/1 parts by volume))
실험 절차
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%).