HCID 53924449, compound → HCID 54573787, compound

Participants

Reaction Steps

The fleshly prepared ethyl 3-ethoxy-2-fluoroacrylate (12, R9 =ethyl, 16.49 g, 0.10 mole) was refluxed in 100 mL of 2N NaOH for 1 hour. After cooling to room temperature, the aqueous solution was washed with hexane (100 mL). The water layer was adjusted to pH 3-4 by addition of 10% HCl and extracted with a mixture of ether and ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and filtered. Evaporation of solvents yielded crude 3-ethoxy-2-fluoroacrylic acid (13, R7 =ethyl, 7.81 g, 0.054 mole) which was dissolved in 53 mL 1N NaOH, then water was evaporated and the residue was dried under vacuum at 85° C. overnight to give the sodium salt (13, R9 =ethyl). This salt was suspended in 100 mL of ether and treated with SOCl2 (4.68 mL, 0.064 mole, 1.2 eq). After reflux for 6 hours, the mixture was concentrated and distilled to give 3-ethoxy-2-fluoroacryloyl chloride (14, R9 =ethyl, bp 102°-107° C./14 mmHg, 6.55 g).

Provenance & Evidence