N,N,N',N'-Tetramethylmethanediamine → 5-((Dimethylamino)methyl)-2-furanmethanol

Participants

Reaction Steps

A solution of bis(dimethylamino)methane (112 g, 1.1 mol) in acetic acid (200 ml) was added dropwise with cooling (10° C.) to a stirred solution of 2-furanmethanol (98 g, 1.0 mol) in acetic acid (1000 ml). The mixture was stirred at room temperature for 18 hours and acetic acid was removed at 60° C. under reduced pressure. Ice (200 g) was added to the residue which was made basic with 40% aqueous sodium hydroxide (with external cooling). The mixture was extracted with ethyl acetate and the extracts were evaporated and distilled to give 5-dimethylaminomethyl-2-furanmethanol (145 g, 94%) b.p. 92°-96° C./0.2 0.5 mmHg.

Provenance & Evidence