Boron trifluoride etherate → HCID 23045064, compound

Participants

Reaction Steps

n-Butyl lithium (1.57M in hexane, 35 ml) was added to a stirred solution of 2-[3-[(2-propynyl)oxy]propyl]pyridine (9.0 g) in dry THF (60 ml) at -78° under nitrogen. Boron trifluoride etherate (6.8 ml) was added and the mixture was stirred at -78° for 30 min. Oxetane (10 ml) was added and after 2 h at -78°, the mixture was treated with more oxetane (10 ml). The dark mixture was allowed to warm to 0°, saturated ammonium chloride (100 ml) was added and the mixture was extracted with ethyl acetate (2×50 ml). The organic layer was washed with brine, dried and concentrated to a dark oil which was purified by FCC eluting with ether to give the title compound as an orange oil (5.1 g), t.l.c. (ethyl acetate-triethylamine 99:1) Rf 0.35.

Provenance & Evidence