Réaction #1361564

Équation de réaction

methanesulfonyl chloride

2-ethyl-1-hydroxy-4-phenylindane

triethylamine

→

aimed product

Rendement 133.4%

2-ethyl-1-hydroxy-2-phenylindane

Rendement 133.4%

Solvants

methylene chloride

—

ice water

methylene chloride

Conditions de réaction

Traitement

1. 1
   AutreTo a 1-liter four-necked round flask (equipped with a stirrer, a dropping funnel
2. 2
   AutreThen, a solution obtained
3. 3
   workup.ADDITIONwas dropwise added slowly to the system
4. 4
   Températurewhile cooling with ice in a nitrogen atmosphere
5. 5
   workup.ADDITIONAfter the addition
6. 6
   Autrethe resulting mixture was reacted for another 3.5 hours at the same temperature
7. 7
   Autrethe organic phase was separated
8. 8
   Extractionthe aqueous phase was further extracted twice with 150 ml of methylene chloride
9. 9
   LavageThe whole organic phase was successively washed with a saturated NaHCO3 solution
10. 10
    Séchagea saturated salt solution, and dried with anhydrous Na2SO4
11. 11
    workup.DISTILLATIONThe solvent was distilled off under reduced pressure
12. 12
    Autrethe residue was separated by silica gel chromatography (developed with hexane)

Mode opératoire

To a 1-liter four-necked round flask (equipped with a stirrer, a dropping funnel and a thermometer) were fed 29.3 g (123.9 mmol) of 2-ethyl-1-hydroxy-4-phenylindane, 51.6 g (371.4 mmol) of triethylamine, 0.75 g (6.3 mmol) of 4-dimethylaminopyridine and 294 ml of methylene chloride. Then, a solution obtained by dissolving 19.2 ml (247.5 mmol) of methanesulfonyl chloride in 19.5 ml of methylene chloride was dropwise added slowly to the system while cooling with ice in a nitrogen atmosphere. After the addition was completed, the resulting mixture was reacted for another 3.5 hours at the same temperature. The reaction mixture was poured in 500 ml of ice water, then the organic phase was separated, and the aqueous phase was further extracted twice with 150 ml of methylene chloride. The whole organic phase was successively washed with a saturated NaHCO3 solution and a saturated salt solution, and dried with anhydrous Na2SO4. The solvent was distilled off under reduced pressure, and the residue was separated by silica gel chromatography (developed with hexane), to obtain 19.7 g of the aimed product (mixture of two kinds of isomers) as a light yellow liquid (yield: 73%).

Source