Reaktion #1576497

Reaktionsgleichung

2-ethyl-1-hydroxy-4-phenylindan

methanesulfonyl chloride

triethylamine

→

aimed product

Ausbeute 73.0%

2-ethyl-4-phenylindene

Ausbeute 73.0%

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 300-ml four-necked round flask (equipped with stirrer chip, dropping funnel and thermometer)
2. 2
   workup.ADDITIONIn a nitrogen atmosphere under ice cooling, to the flask was dropwise added slowly a solution
3. 3
   Sonstigeobtained
4. 4
   Sonstigethe organic phase was separated
5. 5
   Extraktionthe aqueous phase was extracted twice with 50 ml of methylene chloride
6. 6
   workup.ADDITIONby mixing the organic phases together
7. 7
   WaschenThe whole organic phase was washed with a saturated NaHCO3 aqueous solution
8. 8
   Waschenwashed with a saturated saline solution
9. 9
   Trocknenby drying with anhydrous Na2SO4
10. 10
    workup.DISTILLATIONThe solvent was distilled off under reduced pressure
11. 11
    Sonstigethe residue was separated
12. 12
    Sonstigepurified by silica gel chromatography (developed with hexane)

Vorschrift

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

Quelle