Water → HCID 23387257, compound

Participants

Reaction Steps

Alcohol 14 (2.30 g; 19.8 mmol) was dissolved in dry DMF (96 ml) and pyridinium dichromate (PDC) (3.5 eq., 26 g) was added in one portion. The reaction mixture was stirred overnight at room temperature and then poured into 300 ml of water and extracted with (4×80 ml) of ether. The organic layers were combined, washed with brine and concentrated under reduced pressure. The residue was then dissolved in chloroform (30 ml) and the solution was extracted two times with 25 ml of a 10% aqueous solution of NaOH. Combined aqueous phases were then extracted with chloroform (2×25 ml) and acidified with 10% aqueous HCl followed by an extraction with ether (4×50 ml). The combined organic phases were dried over MgSO4, filtered and concentrated under reduced pressure to give the desired product (+,−)-cis-2-ethylcyclopropylacetic acid (15) as a colorless oil (1.7 g, 66%) Characterization: Nmr (1H, 13C), ir, ms

Provenance & Evidence