ethyl 2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]acetate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 61 g (0.244 mol) of crude ethyl 3,6,9,12-tetra-oxa-tridecanoate and 25 ml (0.488 mol) of hydrazine hydrate in 600 ml of ethanol is left to stand for 25 hours at 25°. The reaction mixture is evaporated and the crude, oily 3,6,9,12-tetra-oxa-tridecanoic acid hydrazide, which is thus obtained, is further processed direct. The reaction mixture is evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The product of step (a) (1.5 g) was stirred in a sodium hydroxide solution (0.1M, 30 mL) for 5 hours. The reaction mixture was adjusted to pH 2 by the addition of hydrochloric acid (2M) and then diluted with brine (300 mL). This was extracted with dichloromethane (2×300 mL) and the combined organic layers were dried and the solvent was removed in vacuo. Purification by chromatography on silica gel (Biotage), eluting with 10% methanol in dichloromethane gave the title compound as a clear oil (900 mg). This was extracted with dichloromethane (2×300 mL) the combined organic layers were dried the solvent was removed in vacuo Purification by chromatography on silica gel (Biotage) eluting with 10% methanol in dichloromethane