Potassium Fluoride → HCID 19711317, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3.28 g (20.0 mmol) of 5-bromothiazole (for synthesis see H. C. Beyerman, P. H. Berben, J. S. Bontekoe, Rec. Trav. Chim. 1954, 73, 325), 7.43 mL (22.0 mmol) of (1-ethoxyvinyl)tributyltin, and 284 mg (0.404 mmol) of PdCl2 (PPh3)2 in 40 mL of DMF was heated at 70° C. for 30 h. The reaction mixture was cooled to 0° C. and 40 mL of a solution of potassium fluoride in water and 40 mL of diethyl ether were added. After stirring for 40 min the precipitate was faltered off and the aqueous and organic phases separated. The aqueous phase was re-extracted with 4×40 mL of diethyl ether. The combined ether phases were washed with 2×75 mL of water, 1×100 mL of brine, dried (MgSO4) and the solvent removed in vacuo. Flash chromatography (silica gel, 20% ethyl acetate-hexanes) afforded 2.58 g (83%) of the title compound as a yellow oil: 1H NMR (400 MHz, CDCl3) δ8.65 (s, 1H), 7.80 (s, 1H), 4.61 (d, 1H, J=3 Hz), 4.24 (d, 1H, J=3 Hz), 3.91 (q, 2H, J=7 Hz), 13.9 (t, 3H, J=7 Hz).

Provenance & Evidence