Ethyl Thioglycolate → Ethyl 1-methyl-2-methoxymethylthieno[2,3-d]imidazol-5-yl-carboxylate

反応式

[O-][CH2:2]C.[Na+].[C:5]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:6][SH:7].Cl[C:13]1[N:17](C)[C:16]([CH2:19][O:20][CH3:21])=[N:15][C:14]=1[CH:22]=O>C(O)C>[CH3:2][N:15]1[C:14]2[CH:22]=[C:6]([C:5]([O:9][CH2:10][CH3:11])=[O:8])[S:7][C:13]=2[N:17]=[C:16]1[CH2:19][O:20][CH3:21]

参加物

実験手順

To a freshly prepared sodium ethoxide solution (from 391 mg, 17 mmol of sodium) in 15 mL of ethanol were added dropwise 1.9 mL (2.1 g, 17 mmol) of ethyl thioglycolate. After 1 hour stirring at ambient temperature, 1.6 g (8.5 mmol) of 5-chloro-4-formyl-2-methoxymethyl-1-methylimidazole in 20 mL of absolute ethanol were added and the mixture was heated to 80° C. (analogously to B. Iddon et al., J. Chem. Soc. Perkin Trans. I, 1987, 1457). After 5 hours, the solvent was distilled off, the residue was taken up in 50 mL of methylene chloride and washed with 20 mL of water. The aqueous phase was washed again with 20 mL of methylene chloride and then the combined organic phases were dried with sodium sulfate. After removal of the solvent in vacuo, the crude product obtained was purified by column chromatography (aluminium oxide; methylene chloride). Yield: 1.0 g (46% of theory), C11H14N2O3S (254.31); Rf value: 0.48 (silica gel; methylene chloride/ethanol=50:1); EKA mass spectrum: (M+H)+=255; (M+Na)+=277.