Reaction #696701

Reaction equation

2-ethyl-1-hydroxy-4-phenylindan

triethylamine

methanesulfonyl chloride

→

aimed product

Yield 72.1%

2-ethyl-4-phenylindene

Yield 72.1%

Solvents

methylene chloride

methylene chloride

Conditions

Workup

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

Procedure

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.

Source