Methanol → 5-(Diethoxymethyl)-3-methoxy-2-nitrothiophene
Reaction equation
Br[C:2]1[CH:6]=[C:5]([CH:7]([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10])[S:4][C:3]=1[N+:14]([O-:16])=[O:15].[CH3:17][OH:18].C[O-].[Na+]>>[CH2:9]([O:8][CH:7]([O:11][CH2:12][CH3:13])[C:5]1[S:4][C:3]([N+:14]([O-:16])=[O:15])=[C:2]([O:18][CH3:17])[CH:6]=1)[CH3:10]Participants
4
Conditions
- Temperature
- 120 °C
Procedure
To a solution of 3-bromo-5-(diethoxymethyl)-2-nitrothiophene (Int. 66) (1 g, 3.22 mmol) in MeOH (10 ml) copper(II) oxide (0.051 g, 0.645 mmol), KI (10.7 mg, 0.064 mmol) and sodium methanolate (0.662 g, 12.25 mmol) were added, and the mixture was heated under MW irradiation at 120° C. for 2 hours. The reaction mixture was filtered through a celite pad, the filtrate was concentrated under vacuum and then partitioned between 0.5N HCl and EtOAc. The organic phase was dried over sodium sulfate, filtered and evaporated to give 5-(diethoxymethyl)-3-methoxy-2-nitrothiophene (Int. 67) (680 mg, 2.60 mmol, MS/ESI+261.0 [MH]+). This crude was used without any additional purification.