(R)-4-acetoxycyclopent-2-enone → HCID 59991163, compound

Temperature

-78 °C

n-Propylmagnesium chloride (15.7 ml of a 2M solution in ether, 31.4 mmol) was added slowly to a stirred solution of dimethylzinc (15.7 ml of a 2M solution in toluene, 31.4 mmol) in THF (80 ml) under argon at 0° C. After 30 minutes, the mixture was cooled to −78° C. and (R)-4-acetoxycyclopent-2-enone (4.0 g, 28.5 mmol) in THF (45 ml) was added dropwise over 1 hour. The reaction mixture was stirred for a further 20 minutes and then quenched by the addition of saturated ammonium chloride solution (20 ml). The reaction mixture was allowed to warm to room temperature, diluted with 1N hydrochloric acid (100 ml) and extracted with ether (3×200 ml). The organic layer was washed with brine (200 ml), dried (MgSO4) and the solvent was removed under reduced pressure to yield the acetoxy cyclopentanone 1 as a solution in toluene which was used without further purification in the next step. νmax(film)/cm−1 1740 (C═O).

1. customquenched by the addition of saturated ammonium chloride solution (20 ml)
2. temperatureto warm to room temperature
3. additiondiluted with 1N hydrochloric acid (100 ml)
4. extractionextracted with ether (3×200 ml)
5. washThe organic layer was washed with brine (200 ml)
6. dry with materialdried (MgSO4)
7. customthe solvent was removed under reduced pressure

ORD record

ord-c1792982d93c4215b7c275ea0d6614cb

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06872856B2