4-Thiazolecarboxylic acid, 2-formyl-, ethyl ester

(v) Ethyl 2-formyl-L3-thiazole-4-carboxylate(See, for example, Inami, K., Shiba, T., Bull. Chem. Soc. Jpn., 1985, 58, 352.) Ethyl 2-(diethoxymethyl)-l, 3-thiazole-4-carboxylate (1.34 g, 5.17 mmol; see step(iv) above) was taken up in acetone (100 mL) and a solution of IN HCl (12.8 mL) was then added. The solution was refluxed for 45 min and the solvent removed under reduced pressure. The residue was then dissolved in ethyl acetate (40 mL) and extracted with saturated NaHCOIn a round bottom flask, 2 M HCl (15.3 mL) was added to a solution of 8 (1.85 g, 7.13 mmol) in acetone (153 mL). To a solution of 2-(diethoxymethyl)-1 , 3-thiazole-4-carboxylate (4, 70 g, 270 mmol) in DCM (70 mL) was added TFA (70 mL) at rt. The mixture was stirred at rt overnight then concentrated to dryness. The residue was dissolved in EtOAc and washed with saturated aq. NaHC0To a solution of compound 130 (130 g, 0.50 mol) in acetone (1.3 L) was added 2 N HCl (85 mL, 0.165 mol, 0.33 eq.). The reaction mixture was refluxed (internal temperature about 60 °C), monitored by TLC analysis until starting material was completely consumed (about 1-2 h). Acetone was removed under reduced pressure and the residue was taken up in dichloromethane (1.3 L), washed with saturated NaHCOTo a stirred solution of compound 8 (3.50 g, 20.44 mmol) in glacial acetic acid (50.00 mL), selenium oxide (11.32 g, 102.00 mmol) was added and the reaction was stirred at 100 °C for 24 h. The mixture was cooled down to 25 °C, filtered and volatiles were removed under reduced pressure. Water was added and the aqueous phase was extracted with DCM (3 x 20.00 mL). The combined organic layers were dried over Na

Molecular Weight:185.20
XLogP3:1.3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:185.01466426
Monoisotopic Mass:185.01466426
Topological Polar Surface Area:84.5
Heavy Atom Count:12
Complexity:186
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes