Potassium Phosphate, Tribasic → HCID 59864959, compound

Participants

Reaction Steps

To a magnetically stirred solution of 3-bromo-2-methyl-oct-2-en-4-one (5 gram, 20.54 mmol) (Intermediate IIIc-1) in nitrogen-degassed n-butanol (50 ml) was successively added thiophene-3-boronic acid (3.94 gram, 30.80 mmol), palladium(II)acetate (46.11 mg, 0.21 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (S-Phos) (168.6 mg, 0.41 mmol) and K3PO4 (8.72 g, 41.07 mmol) and the resulting mixture was reacted at 100° C. for 2 hours. The mixture was concentrated in vacuo and purified by sepacore chromatography (40×150 mm column), eluant: (Gradient: eluant 1: petroleum ether (40-60); Eluant 2: petroleum ether (40-60)/diethyl ether=95/5 (v/v)) to give 3-(3-thienyl)-2-methyl-oct-2-en-4-one (2.80 gram, 55%). 1H-NMR (400 MHz, CDCl3) δ 0.83 (t, J=7, 3H), 1.17-1.27 (m, 2H), 1.45-1.54 (m, 2H), 1.72 (s, 3H), 1.97 (s, 3H), 2.30 (t, J=7.4, 2H), 6.92 (br d, J=5, 1H), 7.04 (br d, J=3, 1H), 7.33 (dd, J=5 and 3, 1H).

Provenance & Evidence