Reaction #640095

Reaction equation

3-chloro-2-(chloromethyl)prop-1-ene

tert-butyllithium

4-pyrrolidin-1-ylfuran-2(5H)-one

methanol

→

5-[2-(Chloromethyl)prop-2-en-1-yl]-4-pyrrolidin-1-ylfuran-2(5H)-one

Solvents

pentane

tetrahydrofuran

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture is stirred at −78° C. for a further 30 minutes
2. 2
   Temperaturewarmed to room temperature over a period of about 16 hours
3. 3
   workup.STIRRINGstirred at room temperature for a further 3 hours
4. 4
   Otherthe residue is purified by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm)

Procedure

800 mg (5.22 mmol) of 4-pyrrolidin-1-ylfuran-2(5H)-one (Shandala, M. Y. et al. J. Heterocycl. Chem. 1984, 21, 1753-1754) are dissolved in 80 ml of tetrahydrofuran and cooled to −78° C., and 3.07 ml (5.22 mmol) of a 1.7M solution of tert-butyllithium in pentane are added. After 30 min of stirring at −78° C., 1.21 ml (10.45 mmol) of 3-chloro-2-(chloromethyl)prop-1-ene are added and the mixture is stirred at −78° C. for a further 30 minutes, warmed to room temperature over a period of about 16 hours and stirred at room temperature for a further 3 hours. After addition of methanol and concentration under reduced pressure, the residue is purified by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm) using the mobile phase ethyl acetate. This gives 735 mg (57% of theory) of 5-[2-(chloromethyl)prop-2-en-1-yl]-4-pyrrolidin-1-ylfuran-2(5H)-one.

Source