Methyl iodide → HCID 86346253, compound

5-(2-Methoxycarbonylpropyl)thiophene-2-carboxylic acid tert-butyl ester (13.14 g, 46.3 mmol) was dissolved in tetrahydrofuran (250 mL), 1.09 M lithium bis(trimethylsilyl)azanide/tetrahydrofuran solution (65 mL, 70.9 mmol) was added dropwise at −78° C., and the mixture was stirred for 2 hours. To the reaction mixture was added methyl iodide (11.7 g, 82.4 mmol) at −78° C., and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The residue was added to ethyl acetate and 0.5N-hydrochloric acid solution, the organic layer was separated, and the aqueous layer was extracted two times with ethyl acetate. The organic layers were combined, washed with sodium thiosulfate solution and brine, and dried over anhydrous magnesium sulfate. The solvent of the filtrate after filtration was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound (12.36 g, 41.4 mmol, 89%).

1. stirringthe mixture was stirred at room temperature overnight
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. additionThe residue was added to ethyl acetate and 0.5N-hydrochloric acid solution
4. customthe organic layer was separated
5. extractionthe aqueous layer was extracted two times with ethyl acetate
6. washwashed with sodium thiosulfate solution and brine
7. dry with materialdried over anhydrous magnesium sulfate
8. filtrationThe solvent of the filtrate after filtration
9. customwas evaporated under reduced pressure
10. customThe obtained residue was purified by silica gel column chromatography

ORD record

ord-e29f9e4f4ae34e36ad6b47a35ce0b06f

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227949B2