Acetic Acid → HCID 22254180, compound

Participants

Reaction Conditions

Reaction Steps

(1M in THF) is added to a solution of aldehyde 8 (50 mg, 0.121 mmol), morpholine (2eq) and glacial acetic acid (5 ml) dissolved in THF (5 ml) at room temperature with stirring. The mixture is heated to 70° C. for 18 h, after which, a slow addition of water (1 ml) is used to decompose excess reagent. The mixture is partitioned between ethyl acetate (30 ml) and saturated citric acid solution (10 ml). The organic layer is discarded, and the aqueous layer is carefully basified with 1M aq. sodium hydroxide to pH 9. Then the basic aqueous layer is extracted with ethyl acetate (2×25 ml). The combined organic layers are dried (sodium sulfate), concentrated, and purified by chromatography (silica gel, 10% methanol/methylene chloride) to afford pure product 9 (52% yield).

Provenance & Evidence