Ethanolamine → HCID 22051221, compound

Participants

Reaction Steps

Sodium hydride (1.00 g, 0.025 mmol) was added portionwise to a cooled (0° C.) solution of ethanolamine (1.51 ml, 0.025 mmol) in tetrahydrofuran (25 ml). The reaction mixture was then heated to reflux for 30 minutes. Chloromethylnaphthalene (3.4 ml, 0.0225 mmol) was added and the reaction mixture heated at reflux for a further 3 hours. The reaction mixture was cooled to room temperature and the solvent removed in vacuo. The residue was partitioned between dichloromethane (50 ml) and 1 N aqueous sodium hydroxide (50 ml). The organic phase was separated and the aqueous phase extracted with dichloromethane (2×50 ml). The combined organic extracts were reduced in vacuo and the residue purified by flash column chromatography eluting with dichloromethane:methanol: 880 ammonia (98:2:0.2 changing to 90:10:1 by volume) to give the title compound as a colourless oil (1.80 g, 40%).

Provenance & Evidence