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

HRID 552913Notes

Reaction equation

[N:1]1([C:6]2[CH2:10][O:9][C:8](=[O:11])[CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])(C)(C)C.[Cl:17][CH2:18][C:19]([CH2:21]Cl)=[CH2:20].CO>O1CCCC1.CCCCC>[Cl:17][CH2:18][C:19](=[CH2:20])[CH2:21][CH:10]1[O:9][C:8](=[O:11])[CH:7]=[C:6]1[N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: -78 °C

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.

Workup

stirringthe mixture is stirred at −78° C. for a further 30 minutes
temperaturewarmed to room temperature over a period of about 16 hours
stirringstirred at room temperature for a further 3 hours
customthe residue is purified by column chromatography on silica gel (silica gel 60, Merck, particle size: 0.04 to 0.063 mm)

Sources & evidence

ORD record: ord-076aabea614d4af89bdfae18fb40ed8d
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07951951B2

Reaction notes

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