Triethylamine → Ethyl 2,2-difluoropent-4-enoate

The start of the reaction in the reactor is indicated by a rise in temperature within the reaction chamber 5 from originally -74° C. to about -45° C. During the rest of the reaction period the temperature in the reaction chamber varies from about -45° C. to about -55° C. The reaction mixture from outlet conduit 18 containing the 1,2,2-trifluorovinyl allyl ether is conducted to a stirred solution of 434 g (600 mL, 4.3 mol) of triethylamine in 358 g (450 mL, 7.8 mol) of absolute ethanol cooled in an ice bath. Upon warming to the ice bath temperature, the 1,2,2-trifluorovinyl allyl ether spontaneously rearranges to 2,2-difluoro-4-pentenoyl fluoride, which in the presence of ethanol reacts to yield the desired ethyl 2,2-difluoro-4-pentenoate. The reaction mixture is divided into two equal batches which are treated separately. The following describes the workup of one batch.

1. customThe start of the reaction in the reactor
2. customis indicated by a rise in temperature within the reaction chamber 5 from originally -74° C. to about -45° C
3. customDuring the rest of the reaction period the temperature in the reaction chamber varies from about -45° C. to about -55° C
4. temperaturecooled in an ice bath
5. customreacts

ORD record

ord-4abcc008e00841fbb135759453ba7e96

Source dataset

uspto-grants-1989_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04847401