Dimethylformamide → HCID 57097110, compound

Temperature

25 °C

A 250-mL, one-necked, round bottomed flask equipped with a magnetic stirrer, and under nitrogen, was charged with 1.65 g (14.3 mmol) of alcohol 21 and 40 ml of dry DMF. Pyridinium dichromate 18.8 g (3.5 eq.; 50.1 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 a 10% aqueous HCl. Extraction with ether (4×50 ml), drying over MgSO4, filtration and concentration under reduced pressure afforded the desired compound (1R,2S)-2-ethylcyclopropylacetic acid (22) as a colorless oil (737 mg).

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-b5c2724038bd40f29842aec94766974e

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06458764B1