Methanol → HCID 70612500, compound

Temperature

20 °C

29 g of diketene were added over 20 minutes to a stirred mixture of 39 g of 4-methylcyclohexylamine in 100 ml of tetrahydrofuran and the mixture was stirred at 20° C. for 3 hours. Isopropyl ether was added thereto and the precipitate formed was recovered by vacuum filtration, was washed and dried to obtain 46 g of N-(4-methylcyclohexyl)-acetylacetamide melting at 111° C. A mixture of 46 g of the latter product, 37 g of methyl orthoformate, 1.5 g of p-toluene sulfonic acid and 100 ml of methanol was stirred for 2 hours at 20° C. and after standing for 16 hours, 3 ml of quinoline were added thereto. The mixture was distilled to dryness under reduced pressure and the residue was added to toluene. The stirred mixture was heated at 145° C. for 3 hours while distilling a toluene-methanol azeotrope and was then cooled and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and elution with an 8-2 methylene chloride-acetone mixture gave 24 g of N-(4'-methylcyclohexyl)-3-methoxy-crotonamide melting at 125° C. The RMN spectra showed the product to be the E isomer.

1. waitafter standing for 16 hours
2. distillationThe mixture was distilled to dryness under reduced pressure
3. additionthe residue was added to toluene
4. temperatureThe stirred mixture was heated at 145° C. for 3 hours
5. distillationwhile distilling a toluene-methanol azeotrope
6. temperaturewas then cooled
7. customevaporated to dryness under reduced pressure
8. customThe residue was chromatographed over silica gel and elution with an 8-2 methylene chloride-acetone mixture

ORD record

ord-ca6413362e3f4ef8a56812810df177ff

Source dataset

uspto-grants-1979_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04170465