Sodium Iodide → Methyl cis-7-Iodo-5-heptenoate

Participants

Reaction Steps

To a solution of 31.4 g of cis-7-bromo-5-heptenoic acid, methyl ester in 260 ml of acetone, containing a trace of sodium carbonate was added a solution of 24.7 g of sodium iodide in 260 ml of acetone. A precipitate formed immediately. After 2 minutes, the solution was diluted with 850 ml of ether and filtered. A trace of sodium carbonate was added to the filtrate which was then stripped, redissolved in ether, refiltered, sodium carbonate added and the filtrate stripped, giving 37.9 g of light sensitive product. This product was stored in the cold as a 1M solution in either ether or tetrahydrofuran containing a trace of sodium carbonate and protected from the light. NMR: 5.95-5.2 ppm (2H, m, olefins), 3.85 ppm (2H, d, 7 Hz, ICH2), 3.65 ppm (3H, s, OMe), 2.45-2.0 ppm (4H, m, CH2 --CH2), 1.8 ppm (2H, q, 7 Hz, CH2).

Provenance & Evidence