Trimethylaluminum → 4,6-Dihydrothieno[2,3-b]pyrrol-5-one

Ethyl 2-aminothiophene-3-acetate (100 mg, 0.54 mmol) was dissolved in dry tetrahydrofuran (5 ml) and treated at −78° C. with trimethylaluminium (2M in n-heptane, 0.59 mmol). The reaction mixture was allowed to warm slowly to room temperature over 4 hours, cooled to 0° C. and quenched with saturated aqueous ammonium chloride solution. The solution was extracted with ethyl acetate and the organic phase dried over magnesium sulfate, evaporated to dryness and the residue chromatographed on silica gel using hexane/ethyl acetate (2:1) as eluent to give 45 mg of 4,6-dihydrothieno[2,3-b]pyrrol-5-one as a brown solid. MS(ES): m/e 140 [M+H].

1. temperaturecooled to 0° C.
2. customquenched with saturated aqueous ammonium chloride solution
3. extractionThe solution was extracted with ethyl acetate
4. dry with materialthe organic phase dried over magnesium sulfate
5. customevaporated to dryness
6. customthe residue chromatographed on silica gel

ORD record

ord-e19d464d563141de9198fd02aa0368cd

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06528653B2