Reaction #1361

Reaction equation

water

2-i-butyl-1-hydroxy-4-(1-naphthyl)indene

triethylamine

methanesulfonyl chloride

→

desired product

Yield 93.0%

2-i-butyl-4-(1-naphthyl)indene

Yield 93.0%

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   OtherA 200-ml three-necked round flask equipped with a stirring bar
2. 2
   workup.ADDITIONTo the mixture was added dropwise a solution
3. 3
   Temperaturewhile cooling with ice bath
4. 4
   workup.ADDITIONAfter the addition
5. 5
   Otherwas elevated to room temperature
6. 6
   OtherThereafter, the organic phase was separated
7. 7
   Extractionthe aqueous phase was extracted with 50 ml of methylene chloride
8. 8
   Washwashed with a saturated NaCl aq.
9. 9
   Dryingby dried over anhydrous Na2SO4
10. 10
    OtherThe solvent was evaporated under reduced pressure
11. 11
    OtherThe residue was separated
12. 12
    Otherpurified with silica gel chromatography (eluting with hexane/ethyl acetate (20/1 parts by volume))

Procedure

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%).

Source