1,3-Dimethyl-2-imidazolidinone → (2S,3S)-2-allyl-3-hydroxy-gamma-butyrolactone

Temperature

-45 °C

Lithium hexamethyldisilazide (5.1 ml, 5.1 mmol) was loaded under argon gas in a reaction vessel. (S)-3-Hydroxy-γ-butyrolactone (0.250 g, 2.449 mmol) in THF (5 ml) was added thereto under cooling to −45° C. After stirring for 30 minutes at the same temperature, allyl chloride (0.24 ml, 2,94 mmol) and 1,3-dimethyl-2-imidazolidinone (0.7 ml) in THF (5 ml) was dropped thereto. After stirring for 30 minutes at the same temperature, an aqueous saturated ammonium chloride was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, and condensed in vacuo. The residue was purified by silica gel chromatography to give (2S,3S)-2-allyl-3-hydroxy-γ-butyrolactone (0.261 g, yield 75%).

1. additionwas dropped
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with water and saturated brine
4. dry with materialdried over magnesium sulfate, and condensed in vacuo
5. customThe residue was purified by silica gel chromatography

ORD record

ord-bbbe6aecca904c5398a997f0604282ad

Source dataset

uspto-grants-2001_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06268515B1