Methanol → HCID 70612508, compound

Temperature

145 °C

A solution of 13.5 g of diketene in 50 ml of tetrahydrofuran was added to a mixture of 18 g of 1-methylcyclohexylamine and 180 ml of tetrahydrofuran and the mixture was stirred at 10° C. for 4 hours. The mixture was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with an 8-2 methylene chloride-acetone mixture gave 28 g of N-(1-methylcyclohexyl)acetylacetamide with a refractive index of ND23 =1.4865. 6 g of the latter product and 0.2 g of p-toluene sulfonic acid were added to a mixture of 5 g of methyl orthoformate and 10 ml of methanol. The mixture was stirred and allowed to stand for 16 hours at 20° C. 6.5 ml of quinoline were added and the mixture was evaporated to dryness under reduced pressure. The residue was added to toluene and the mixture was heated at 145° C. for 3 hours while distilling a toluene-methanol azeotrope. The mixture was evaporated to dryness under reduced pressure and the residue was chromatographed over silica gel. Elution with an 8-2 methylene chloride-acetone mixture gave 4 g of N-(1'-methylcyclohexyl)-3-methoxy-crotonamide melting at 105° C. The RMN spectra showed the product to be the E isomer.

1. customthe mixture was evaporated to dryness under reduced pressure
2. additionThe residue was added to toluene
3. distillationwhile distilling a toluene-methanol azeotrope
4. customThe mixture was evaporated to dryness under reduced pressure
5. customthe residue was chromatographed over silica gel
6. washElution with an 8-2 methylene chloride-acetone mixture

ORD record

ord-b6caa6f8ad5a468dac41150e12902527

Source dataset

uspto-grants-1979_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04170465