Tetrahydrofuran → HCID 10089452, compound

Participants

Reaction Conditions

Reaction Steps

A stirring solution of 1 (2.0 g, 6.04 mmol) in 40 mL of THF was cooled to -78° C. followed by the addition of n-BuLi (1.6M, 4.32 mL, 6.91 mmol). The mixture was stirred at -78° C. for 30 minutes and treated with furalaldehyde (670 mg, 6.97 mmol) and then slowly warmed to room temperature and diluted with 16 mL of water. The mixture was then extracted with ether (200 mL×2) and the combined extracts were washed with brine (saturated, 50 mL) and dried (Na2SO4). The extracts were concentrated to give the crude product (2.5 g), which was purified by HPLC with 20% EtOAc/heptane to yield Compounds 13, 14a and 14b as follows:

Provenance & Evidence