N-Methoxy-N-methylpropionamide → HCID 22473751, compound

Temperature

-70 °C

A solution of 3-bromo-4-methylbenzo[b]thiophene (1.69 g) in tetrahydrofuran (10 ml) was added dropwise under nitrogen at −70° C. over 10 minutes to a stirred solution of n-butyllithium (2.5M solution in hexanes; 3.87 ml) in ether (30 ml), then the mixture was stirred at −70° C. for 30 minutes. A solution of N-methoxy-N-methylpropionamide (1.31 g) in tetrahydrofuran (10 ml) was added dropwise at −70° C. over 10 minutes, the mixture was stirred at −70° C. for 3 hours, then it was allowed to warm to ambient temperature and quenched by the addition of saturated aqueous ammonium chloride solution (30 ml). The organic layer was separated, washed with saturated aqueous sodium chloride solution (30 ml), and dried (MgSO4). The solvents were removed in vacuao to give 1-(4-methylbenzo[b]thiophen-2-yl)propan-1-one (0.53 g) as an orange solid which was used without further purification.

1. stirringthe mixture was stirred at −70° C. for 3 hours
2. temperatureto warm to ambient temperature
3. customquenched by the addition of saturated aqueous ammonium chloride solution (30 ml)
4. customThe organic layer was separated
5. washwashed with saturated aqueous sodium chloride solution (30 ml)
6. dry with materialdried (MgSO4)
7. customThe solvents were removed in vacuao

ORD record

ord-aa8be48533d54085a1117758a789f9cb

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06900216B2