Ethylene Oxide → HCID 21875084, compound

Participants

Reaction Steps

A solution of n-butyllithium in hexane (1.55M, 100 ml) was added over 5 min to a stirred solution of furan (10 g) and tetramethylethylenediamine (17.4 g) in dry THF (100 ml) at 0° under nitrogen. The mixture was stirred for 2 h at 0°, treated with iodopropane (25 g) over 15 min at 0° (reaction exothermic), and stirred at 0° for 1 h and at 23° for 1 h. The mixture was cooled to 0°, n-butyllithium (1.55M, 100 ml) was added over 10 min and the mixture stirred at 0° for a further 1 h. The mixture was cooled to -10°, treated with a solution of ethylene oxide (7 g) in dry THF (20 ml) over 15 min and stirred at -10° to 0° for 2 h and at 23° for 18 h. Water (200 ml) was added, the organic solvents removed in vacuo and the residue extracted with ether (3×200 ml). The extracts were washed with 0.5M hydrochloric acid (200 ml), 8% sodium bicarbonate (50 ml) and brine (50 ml), dried and evaporated in vacuo to give a brown oil which was distilled (Kugelrohr) to give the title compound as a pale-yellow oil (18.2 g) b.p. 191°-200°/15 Torr.

Provenance & Evidence