Formaldehyde → (+/-) 5-(2-Thienyl)-3-(methoxycarbonyl-o-chlorobenzyl)-1,3-oxazoline

Participants

Reaction Conditions

Reaction Steps

Methyl N-(2-(2-thienyl)-2-hydoxyethyl)-2-o-chlorophenylglycinate (21) (2.5 g, 7.6 mmol) was dissolved in ethanol and treated with 37% formaline (1.85 g, 22.8 mmol), then heated at 40° C. over the night under nitrogen. The ethanol is evaporated under vacuum and the residual water was removed by azeotropic distillation with toluene to provide 2.3 g of desired product as a mixture of diastereoisomers. 1H-NMR (CDCl3, ppm) 7.72 (1H, m), 7.43 (1H, m), 7.2-7.3 (2H, m), 7.15 (1H, m), 6.95 (2H, m), 5.35 (1H, q), 5.15 and 5.05 (2H, 2s), 4.55 (2H, q), 4.40 (2H, q), 3.75 and 3.70 (3H, 2s), 3.3-3.5 (1H, m), 2.9-3.1 (1H, m).

Provenance & Evidence