反应详情

To a solution of ethyl 2-azidoethoxyacetate (6.56 g, 37.9 mmol) in MeOH (80 ml) was added 1N aq. NaOH (80 ml) and the mixture was stirred at room temperature overnight (17 h). After removing the insoluble material, the methanol was evaporated in vacuo and this was saturated with sodium chloride and washed with ether (30 ml×3). The aqueous layer acidified with 3N HCl (30 ml) was extracted with ether (40 ml×4). The ether extracts were washed with brine, dried (MgSO4) and evaporated to yield 4.25 g (29.3 mmol, 77.3%) of 2-azidoethoxyacetic acid as a colourless oil: 1Hmr (CDCl3) δ: 3.3-4.0 (4H, m, --OCH2CH2N3), 4.22 (2H, s, --COCH2O--), 9.52 ppm (1H, s, --CO2H, exchanged with D2O); ir (neat) νmax : 2600-3300 (br,--CO 2 H) 2100 (azide) and 1740 cm-1C=O-CO2H). This material was used in the next step without further purification.

1. customAfter removing the insoluble material
2. customthe methanol was evaporated in vacuo
3. washthis was saturated with sodium chloride and washed with ether (30 ml×3)
4. extractionwas extracted with ether (40 ml×4)
5. washThe ether extracts were washed with brine
6. dry with materialdried (MgSO4)
7. customevaporated