Methyl iodide → Methyl (1-methyl-1,2,3,4-tetrahydro-1-naphthalenyl)(oxo)acetate

Temperature

70 °C

Ethyl (2Z)-3,4-dihydro-1(2H)-naphthalenylidene(formylamino)ethanoate (1.31 g, 5.05 mmol, from Reference Example 9) is refluxed with 6N HCL (10 mL) for 1 hour. The mixture is evaporated, dried and the residue taken up in tetrahydrofuran (8 mL) and water (1.7 mL). To this is added 5 N sodium hydroxide solution (3.6 mL, 18.0 mmol) and iodomethane (0.9 mL, 14.5 mmol). While stirring under a nitrogen atmosphere, the reaction mixture is heated in a 70° C. oil bath for 5½ hours. Additional volumes of 5 N sodium hydroxide solution (2.0 mL) and iodomethane (0.3 mL, 4.8 mmol) are added. The reaction mixture is allowed to stir for 2 days at room temperature, then evaporated in vacuo to remove most of the tetrahydrofuran. This is extracted with ethyl acetate and the organic layer then dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give a clear oil, 0.49 g, MS: m/z 233.2 (M+1).

1. customThe mixture is evaporated
2. customdried
3. stirringto stir for 2 days at room temperature
4. customevaporated in vacuo
5. customto remove most of the tetrahydrofuran
6. extractionThis is extracted with ethyl acetate
7. dry with materialthe organic layer then dried over anhydrous sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated in vacuo
10. customto give a clear oil, 0.49 g, MS

ORD record

ord-235324eccf9049c3bde33720681df7f7

Source dataset

uspto-grants-2008_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07390910B2