تفاعل #696701

معادلة التفاعل

2-ethyl-1-hydroxy-4-phenylindan

triethylamine

methanesulfonyl chloride

→

aimed product

المردود 72.1%

2-ethyl-4-phenylindene

المردود 72.1%

المذيبات

methylene chloride

methylene chloride

ظروف التفاعل

المعالجة

1. 1
   أخرىTo a 300-ml four-necked round flask (equipped with a stirrer tip, a dropping funnel
2. 2
   workup.ADDITIONAfter the dropwise addition
3. 3
   أخرىthe organic phase was separated
4. 4
   استخلاصthe aqueous phase was extracted twice with 50 ml of methylene chloride
5. 5
   غسيلThe combined organic phases were washed with a saturated NaHCO3 aqueous solution
6. 6
   تجفيفby drying over anhydrous Na2SO4
7. 7
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
8. 8
   أخرىthe residue was purified by silica gel chromatography

الإجراء التجريبي

To a 300-ml four-necked round flask (equipped with a stirrer tip, a dropping funnel and a thermometer) were introduced 9.78 g (41.3 mmol) of 2-ethyl-1-hydroxy-4-phenylindan, 17.2 ml (123.8 mmol) of triethylamine, 0.25 g (2.1 mmol) of 4-dimethylaminopyridine and 98 ml of methylene chloride, and then in a nitrogen atmosphere under ice cooling, a solution of 6.4 ml (82.5 mmol) of methanesulfonyl chloride in 6.5 ml of methylene chloride was dropwise added slowly. After the dropwise addition was completed, the reaction was performed for further 3.5 hours at the same temperature. The reaction mixture was poured into 250 ml of ice water, the organic phase was separated, and the aqueous phase was extracted twice with 50 ml of methylene chloride. The combined organic phases were washed with a saturated NaHCO3 aqueous solution and then with a saturated saline solution, followed by drying over anhydrous Na2SO4. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography using hexane to obtain 6.56 g of the aimed product (a mixture of isomers) as a light yellow liquid (yield: 73%). The properties of the product thus obtained are described below.

المصدر