Acetic Acid → Ethyl 2-cyano-4,4-dimethylpent-2-enoate

A mixture of pivaldehyde (5.00 g, 58 mmol), ethylcyanoacetate (6.60 g, 58.3 mmol), acetic acid (3.50 g, 58.3 mmol) and pyridine (4.60 g, 58.2 mmol) was heated at reflux for 1 h. A second portion of pivaldehyde (5.00 g, 58 mmol) was added. The refluxing of the mixture was continued for 18 h. After cooling, the mixture was poured into 1N aqueous HCl (50 mL). The resulting mixture was extracted with EtOAc (3×50 mL). The combined organic layers were washed with 1N aqueous HCl, dried (MgSO4) and concentrated to give a colorless oil. The oil was purified by flash chromatography on SiO2 using hexane-EtOAc (9:1) as the eluant to give 2-cyano-4,4-dimethyl-2-pentenoic acid ethyl ester as a colorless oil (7.69 g, 73% yield).

1. temperaturewas heated
2. temperatureat reflux for 1 h
3. temperatureThe refluxing of the mixture
4. temperatureAfter cooling
5. extractionThe resulting mixture was extracted with EtOAc (3×50 mL)
6. washThe combined organic layers were washed with 1N aqueous HCl
7. dry with materialdried (MgSO4)
8. concentrationconcentrated
9. customto give a colorless oil
10. customThe oil was purified by flash chromatography on SiO2

ORD record

ord-2ff28f7b1d7440c582bfce3e572a176e

Source dataset

uspto-grants-1995_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05380727