Potassium Carbonate → Methyl 16-iodo-4-thia-hexadecanoate

Participants

Reaction Steps

1,12-diiodododecane (2.66 g, 6.3 mmol) was dissolved in 20 mL acetonitrile. Methyl 3-mercaptopropionate (0.76 g, 6.3 mmol) and K2CO3 (1.1 g, 8 mmol) were added and the mixture was allowed to react at room temperature for 20 h. The mixture was acidified with ice-diluted HCl and the solution was extracted twice with ether (20 mL). The combined ether fractions were washed successively with dilute NaHCO3, water and brine, dried (MgSO4 and evaporated under reduced pressure. The product 1 (0.84 g, 32% yield) was isolated by column chromatography (hexane/ethyl acetate 9:1) and recrystallized in MeOH. TLC (hexane/ethyl acetate 9:1) Rf=0.4. Melting point=33° C. 1H-NMR δ1.4 (m, 20H, CH2), 2.52 (t, 2H, C(2)H2), 2.61 (t, 2H, C(5)H2), 2,79 (t, 2H, C(3)H2), 3.20 (t, 2H, C(16)H2), 3.71 (s, 3H, —COO—CH3).

Provenance & Evidence