Dimethylformamide → HCID 54225508, compound

Temperature

25 °C

A 250-mL, one-necked, round bottomed flask equipped with a magnetic stirrer, and under nitrogen, was charged with 1.7 g (14.9 mmol) of alcohol 23 and 40 ml of dry DMF. Pyridinium dichromate 19.6 g (3.5 eq.; 52.1 mmol) was added in one portion. The reaction mixture was stirred overnight at 25° C. and then poured into 200 ml of water and extracted with ether (4×80 ml). The organic layers were concentrated under reduced pressure, and the residue was then dissolved in chloroform (50 ml) and extracted with a 10% aqueous NaOH (2×25 ml). The combined aqueous layers were washed twice with 25 ml of chloroform, followed by acidification with 10% aqueous HCl. Extraction with ether (4×50 ml), drying over MgSO4, filtration and concentration under reduced pressure afforded the desired compound (1R,2R)-2-ethylcyclopropylacetic acid (24) as a colorless oil (1.05 g).

1. customA 250-mL, one-necked, round bottomed flask equipped with a magnetic stirrer
2. extractionextracted with ether (4×80 ml)
3. concentrationThe organic layers were concentrated under reduced pressure
4. dissolutionthe residue was then dissolved in chloroform (50 ml)
5. extractionextracted with a 10% aqueous NaOH (2×25 ml)
6. washThe combined aqueous layers were washed twice with 25 ml of chloroform
7. extractionExtraction with ether (4×50 ml)
8. dry with materialdrying over MgSO4, filtration and concentration under reduced pressure

ORD record

ord-a31b85f814f04cc2ae7d9f3eaa4529cc

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06458764B1