2-Thiophenecarboxaldehyde → HCID 23369385, compound

Reaction equation

Cl.[NH2:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH:14]=O.[BH3-]C#N.[Na+]>CO>[S:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH2:14][NH:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6]

Participants

Procedure

To a stirring 25 mL MeOH solution of 1.40 g (10 mmol) of methyl β-alaninate hydrochloride and 1.34 g (12 mmol) of thiophene carboxaldehyde was added 1.26 g (20 mmol) of NaCNBH3. After 1 hour, 25 mL of saturated KHCO3 was added to the reaction. The reaction mixture was then filtered, and the resulting filtrate was extracted with 50 mL of DCM. The organic layer was treated as described above in Example 7, and the residue was chromatographed to yield 0.60 g (30%) of product. Analysis calculated for C9H13NO2S (M.W. 199.27): C, 54.25; H, 6.58; N, 7.03. Found: C, 54.02; H, 6.63; N, 6.77.