Formic Acid → Ethyl 1-(2-Hydroxyethyl)-1,2,3-triazole-4-carboxylate

A solution of ethanolamine (60 ml, 1 mole) in methanol (320 ml) at 5° was treated with formic acid until a pH of 5 was obtained. A solution of ethyl α-formyldiazoacetate (crude, approximately 0.3 mole) in methanol (320 ml) was then added and the mixture stirred at room temperature for two days. The mixture was then evaporated, chloroform (1 liter), then water (200 ml) was added and the mixture was treated with sodium bicarbonate until a pH of 7 was reached. The phases were separated and the aqueous phase saturated with sodium chloride and extracted with chloroform (6 x 300 ml). The combined organic phases were dried (MgSO4), filtered and evaporated. The residue was then dissolved in toluene (approximately 100 ml). The resulting crystalline solid was filtered, washed with ether and dried to provide the title compound (41.6 g) as a solid; λmax (nujol) 3320, 3140, 1725 cm-1 ; δ (CDCl3), 1.38 (3H, t, J 7.5Hz), 4.00-4.80 (7H, m, becomes 6H, m on D2O exch), 8.40 (1H, s). This material was pure enough for further synthetic progression.

1. customwas obtained
2. customThe mixture was then evaporated
3. additionchloroform (1 liter), then water (200 ml) was added
4. additionthe mixture was treated with sodium bicarbonate until a pH of 7
5. customThe phases were separated
6. extractionthe aqueous phase saturated with sodium chloride and extracted with chloroform (6 x 300 ml)
7. dry with materialThe combined organic phases were dried (MgSO4)
8. filtrationfiltered
9. customevaporated
10. dissolutionThe residue was then dissolved in toluene (approximately 100 ml)
11. filtrationThe resulting crystalline solid was filtered
12. washwashed with ether
13. customdried

ORD record

ord-e2d51c2bd85f446780ccbd73be053ad1

Source dataset

uspto-grants-1990_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04931434