Potassium Carbonate → Methyl 5,6-dimethoxy-1-benzothiophene-2-carboxylate

HRID 2175700Notes

Reaction equation

F[C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[CH:4]=O.[SH:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:13][O:12][C:7]1[C:8]([O:10][CH3:11])=[CH:9][C:2]2[S:14][C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:4][C:3]=2[CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of 2-fluoro-4,5-dimethoxybenzaldehyde (1.10 g, 6 mmol) in DMF (50 mL) was added methyl 2-mercaptoacetate (0.58 mL, 6.6 mmol) and potassium carbonate (2.48 g, 18 mmol). The resulting mixture was then heated at 60° C. for 15 hours. The DMF was removed via rotary evaporation and the residue was diluted with water and extracted with DCM. The organic phase was dried over sodium sulfate and the solvent was removed under reduced pressure to afford methyl 5,6-dimethoxybenzo[b]thiophene-2-carboxylate as a light yellow solid (1.0 g, 67%). LC-MS (ES-API); rt 8.48 min; m/z calculated for C12H12O4S [M+Na]+ 275.0, found 275.0.

Workup

customThe DMF was removed via rotary evaporation
additionthe residue was diluted with water
extractionextracted with DCM
dry with materialThe organic phase was dried over sodium sulfate
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-6c378ed51af043e88ec30e138ede6ecd
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062076B2

Reaction notes

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