HCID 15544964, compound → HCID 9855496, compound

Temperature

-78 °C

Methylmagnesium chloride (7.1 ml of a 3M solution in ether, 21.3 mmol) was added slowly to a stirred solution of dimethylzinc (5.3 ml of a 2M solution in toluene, 10.6 mmol) in THF (80ml) under argon at 0° C. After 30 minutes the mixture was cooled to −78° C. and 2 (1.2 g, 9.7 mmol) in THF (45 ml) was added dropwise over 1 hour. The reaction mixture was stirred for 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 4 as a solution in toluene which was purified by column chromatography (SiO2, pentane-ether, 1:0 to 9:1 to give the cyclopentanone 4 (0.86 g, 63%). νmax(CDCl3)/cm−1 1733 (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
8. customto yield 4 as a solution in toluene which
9. customwas purified by column chromatography (SiO2, pentane-ether, 1:0 to 9:1

ORD record

ord-78d1ef353a6347709ecba54ecae53a06

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06872856B2