Methyl iodide → Methyl 4-methoxy-2-methylacetoacetate

Methyl 4-(methyloxy)-3-oxobutanoate (2.0 g, 13.69 mmol) was dissolved in tetrahydrofuran (THF) (14 mL), cooled in an ice bath and treated portionwise with 60% sodium hydride in mineral oil (0.547 g, 13.69 mmol). The resulting mixture was allowed to warm to room temperature over 25 minutes and then treated dropwise with a solution of methyl iodide (0.856 mL, 13.69 mmol) in tetrahydrofuran (THF) (2 mL). The resulting mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure and the residue was taken up in ethyl acetate and washed with water. The organic layer was separated, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (SP4, 40+M) eluting with a gradient of 0-50% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound as a colourless oil. (1.01 g);

1. temperaturecooled in an ice bath
2. customThe solvent was removed under reduced pressure
3. washwashed with water
4. customThe organic layer was separated
5. customdried under magnesium sulfate
6. customevaporated under reduced pressure
7. customThe residue was purified by column chromatography (SP4, 40+M)
8. washeluting with a gradient of 0-50% ethyl acetate and iso-hexane
9. additionProduct containing fractions
10. customevaporated under reduced pressure

ORD-Eintrag

ord-b9f3846083d04e80b9071afbd3ba0b64

Quelldatensatz

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08796283B2