Reaction #1951043

Reaction equation

tosyl chloride

isopentenol

hexane

→

3-methyl-3-butene-1-yl tosylate

Yield 85.3%

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   Otheris equipped
2. 2
   Otherhas been carefully dried
3. 3
   workup.ADDITIONare slowly added to this mixture through a septum
4. 4
   Otherresulting in the immediate formation of a white precipitate
5. 5
   FiltrationThe mixture is then filtered
6. 6
   Concentrationthe filtrate concentrated by evaporation under reduced pressure
7. 7
   workup.ADDITIONThe solution is then diluted with diethyl ether
8. 8
   OtherOnce the solvent has evaporated
9. 9
   Othera yellowish oil is obtained
10. 10
    OtherThe product is purified by preparative chromatography through a silica column (silica gel 60; eluent: pentane/ethyl acetate 85/15)

Procedure

2.32 mmol (442 mg) of tosyl chloride and 2.55 mmol (312 mg) of 4-(N,N-dimethylamino)pyridine are introduced while stirring with a magnetic stirrer into 5 ml of anhydrous dichloromethane in a glass reaction vessel which is equipped for handling under an inert atmosphere and has been carefully dried. 2.32 mmol (200 mg) of isopentenol dissolved in approx. 1 ml of dichloromethane are slowly added to this mixture through a septum using a syringe. The reaction is monitored by thin-layer chromatography on silica (silica gel 60 F-254; eluent: pentane/ethyl acetate 85/15 vol./vol.; Rf (product)=0.4 and Rf (TsCl)=0.5). After approx. 3 hours' stirring under a nitrogen atmosphere, the reaction mixture is diluted in a large volume of hexane (approx. 100 ml), resulting in the immediate formation of a white precipitate. The mixture is then filtered and the filtrate concentrated by evaporation under reduced pressure. The solution is then diluted with diethyl ether and refiltered. Once the solvent has evaporated, a yellowish oil is obtained. The product is purified by preparative chromatography through a silica column (silica gel 60; eluent: pentane/ethyl acetate 85/15). In this manner, 1.98 mmol (475 mg) of 3-methyl-3-butene-1-yl tosylate (85% isolated yield) are obtained. The compound (colorless oil) is stored at +4° C. in an anhydrous medium.

Source