Ethylene Oxide → HCID 21875084, compound

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.

1. custom(reaction exothermic)
2. stirringstirred at 0° for 1 h and at 23° for 1 h
3. temperatureThe mixture was cooled to 0°
4. stirringthe mixture stirred at 0° for a further 1 h
5. temperatureThe mixture was cooled to -10°
6. stirringstirred at -10° to 0° for 2 h and at 23° for 18 h
7. customthe organic solvents removed in vacuo
8. extractionthe residue extracted with ether (3×200 ml)
9. washThe extracts were washed with 0.5M hydrochloric acid (200 ml), 8% sodium bicarbonate (50 ml) and brine (50 ml)
10. customdried
11. customevaporated in vacuo
12. customto give a brown oil which
13. distillationwas distilled (Kugelrohr)

ORD record

ord-e3ba5b3abaf742699284ed7fd703fa9f

Source dataset

uspto-grants-1991_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05039697