Water → Methyl 5-methoxypent-4-enoate

Temperature

-78 °C

34.3 g (0.1 mole) methoxymethyltriphenylphosphonium chloride was suspended in 100 ml dry tetrahydrofuran and cooled to -78° C. under argon. 75 ml (0.1 mole) n-butyllithium solution in hexane was added and the solution allowed to warm to room temperature. After cooling to -78° C. 12.1 g (0.0105 moles) methyl 4-oxobutanoate was added in 50 ml tetrahydrofuran. The solution was allowed to reach room temperature then poured into water and extracted twice with ether. The ether extracts were washed with saturated sodium chloride solution dried and concentrated in vacuo. This was eluted through 250 g silica gel with 1 l ether-hexane 1:1 to give a faintly yellow liquid 9.2 g containing both (Z) and (E) enol ethers.

1. temperatureto warm to room temperature
2. temperatureAfter cooling to -78° C
3. customto reach room temperature
4. extractionextracted twice with ether
5. washThe ether extracts were washed with saturated sodium chloride solution
6. customdried
7. concentrationconcentrated in vacuo
8. washThis was eluted through 250 g silica gel with 1 l ether-hexane 1:1

ORD record

ord-db15010c44024ab7b6dce45226590289

Source dataset

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05246966