Diethyl Ether → HCID 20452089, compound

Participants

Reaction Steps

A mixture of ethyl 2-chloroethoxyacetate (7.71 g, 36.3 mmol) and sodium azide (3.31 g, 50.9 mmol) in DMF (100 ml) was heated at 80°-90° C. for 3.5 h by which time tlc (hexane; ether 1:1) indicated that the reaction was complete. The cooled mixture was poured into H2O (1 l) and extracted with ether (250 ml×3). The extracts washed with H2O (×2) and brine (×1) were dried (MgSO4) and evaporated yielding 7.16 g (41.4 mmol 89.4%) of ethyl 2-azidoethoxyacetate as a yellowish oil: 1Hmr (CDCl3) δ: 1.30 (3H, t, J=7 Hz, --OCH2CH3), 3.3-4.0 (4H, m, --OCH2CH2N3), 4.13 (2H, s, --COCH2O--), 4.23 ppm (2H, q, J=7 Hz, --OCH2CH3); ir (neat) νmax : 2100 (N3) and 1750 cm-1 (C=O ester). This material was used in the next step without further purification.

Provenance & Evidence