Water → HCID 23387257, compound

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

1. extractionextracted with (4×80 ml) of ether
2. washwashed with brine
3. concentrationconcentrated under reduced pressure
4. dissolutionThe residue was then dissolved in chloroform (30 ml)
5. extractionthe solution was extracted two times with 25 ml of a 10% aqueous solution of NaOH
6. extractionCombined aqueous phases were then extracted with chloroform (2×25 ml)
7. extractionfollowed by an extraction with ether (4×50 ml)
8. dry with materialThe combined organic phases were dried over MgSO4
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure

ORD record

ord-f4e0aa8b531c419fa9d2dda6197964a2

Source dataset

uspto-grants-2002_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06458764B1