Thiirane → 4-Hydroxymethyl-1-(2-mercaptoethyl)pyridinium trifluoromethanesulfonate

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-pyridinemethanol (1.635 g, 0.015 mol) in 10 mL of CH2Cl2, at 0° C. under N2, was added dropwise trifluoromethanesulfonic acid (1.327 mL, 0.015 mol). A yellow-brown oil rapidly separated out. An additional equivalent of 4-pyridinemethanol (1.635 g, 0.015 mol) was added to this mixture and the solvent was removed under reduced pressure to give an oil. To this oil was added ethylene sulfide (0.891 mL, 0.015 mol) and the resulting homogeneous mixture was heated (oil bath) at about 60° C. for 3 h. The reaction mixture was then taken up in 15 mL of H2O and the aqueous solution was washed with CH2Cl2 (5×5 mL). After removing residual organic solvent in vacuo the aqueous solution was applied to a C18 reverse-phase column. Elution with H2O and subsequent evaporation of the relevant fractions afforded an oil which was further dried in vacuo over P 2 O5 to give the product (4.64 g, 97%) as a colourless oil. ir (film) νmax : 3455 (s, OH), 2565, (w, SH) cm-1 ; 1Hnmr (d6 -acetone) δ: 9.07, 8.18 (ABq, J=6.8 Hz, 4H, aromatic), 5.03 (s, 2H, CH2OH), 4.96 (t, J=6.5 Hz, 2H, N--CH2), 4.09 (br s, 1H, --OH), 3.5-3.1 (m, 2H, S--CH2), 2.25 (brs, 1H, --SH).

Provenance & Evidence