Water → (E)-4-morpholino-2-buten-1-ol

Participants

Reaction Conditions

Reaction Steps

Tetrahydrofuran (15 ml) was added to 70% solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene (49.7 g) under an atmosphere of nitrogen and then cooled. A solution of 4-morpholino-2-butyn-1-ol (3.0 g) in tetrahydrofuran (15 ml) was added dropwise maintaining the reaction temperature 4-5° C. After being stirred for 10 minutes, the reaction mixture was allowed to warm room temperature. After 1 hour, water (6 ml) and 10% aqueous sodium hydroxide solution (4.5 ml) were added cautiously and then filtered. The filtrate was dried over potassium carbonate and concentrated under reduced pressure to give an oily product, which was purified by column chromatography on silica gel using ethyl acetate-methanol (5:1) to afford (E)-4-morpholino-2-buten-1-ol (1.08 g).

Provenance & Evidence