Aluminium lithium hydride → HCID 69180016, compound

Participants

Reaction Steps

Lithium aluminium hydride (1.7 g) was added batchwise to 8-isocyanato-8-thiophen-3-yl-1,4-dioxa-spiro[4.5]decane (6 g; 22.6 mmole) dissolved in dry THF (70 ml) at 0 to 5° C. The reaction mixture was stirred for about 1.5 hours under reflux. On completion of the reaction (reaction monitored by thin layer chromatography), excess lithium aluminium hydride was destroyed with saturated aqueous sodium sulfate solution (20 ml). The resultant precipitate was filtered out over Celite. The filtrate was concentrated and extracted with ethyl acetate (3×100 ml). The organic phase was separated, dried (sodium sulfate) and concentrated under vacuum. Purification by column chromatography (silica gel, 50% ethyl acetate in n-hexane) yielded 2.5 g methyl-(8-thiophen-3-yl-1,4-dioxa-spiro[4.5]dec-8-yl)-amine (43%; white low-melting solid).

Provenance & Evidence