Dimethylformamide → HCID 54225508, compound

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence