Triethyl phosphonoacetate → (E)-Ethyl 3-cyclobutylacrylate

Temperature

0 °C

To a suspension of lithium chloride (2.22 g, 52.2 mmol) in MeCN (80 mL) were added ethyl 2-(diethoxyphosphoryl)acetate (available from Aldrich) (8.37 mL, 41.8 mmol) and DBU (16.7 mL, 111 mmol) at room temperature. The mixture was cooled to 0° C., and to it was added cyclobutanecarbaldehyde 70.B (2.93 g, 34.8 mmol) dropwise. The resulting cloudy mixture was warmed to room temperature and stirred overnight. The mixture was partitioned between water and EtOAc. The layers were separated, and the aqueous phase was extracted with additional EtOAc. The combined organic layers were washed with water and brine, dried (MgSO4), and concentrated. The residue was purified by silica gel flash chromatography (0-10% EtOAc/hexane) to afford (E)-ethyl 3-cyclobutylacrylate 70.C as a colorless liquid (5.00 g, 94%).

1. temperatureThe resulting cloudy mixture was warmed to room temperature
2. customThe mixture was partitioned between water and EtOAc
3. customThe layers were separated
4. extractionthe aqueous phase was extracted with additional EtOAc
5. washThe combined organic layers were washed with water and brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated
8. customThe residue was purified by silica gel flash chromatography (0-10% EtOAc/hexane)

ORD record

ord-6a7b0f6c26ab4ee99e6382156fa2025b

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08030354B2