Tetrahydrofuran → HCID 54490614, compound

Participants

Reaction Steps

To a stirred suspension of 3-(hydroxypropyl)triphenylphosphonium bromide (10.5 g) in dry THF (100 ml) at 0°, under nitrogen was added n-butyllithium (1.8 M in hexane, 30 ml). The stirring was continued at 0° for 30 min then a solution of 3,5-dimethyl-4-nitrobenzaldehyde (4.5 g) in dry THF (50 ml) was added over 10 min. The mixture was stirred at -10° for 1 h and at 0° for 1 h, saturated ammonium chloride (50 ml) was added and the mixture was extracted with EA (3×50 ml) the organic extracts were washed with water, brine, dried, concentrated and purified by [FCS] (triethylamine deactivated silica) eluting with EA-methanol (9:1) gave the title compound (0.3 g). T.l.c. (Toluene:ethanol:0.88 ammonia solution 39:10:1) Rf 0.18.

Provenance & Evidence