Reaktion #1670694

Reaktionsgleichung

Trifluoromethanesulfonic acid

3-pyridinemethanol

ethylene sulfide

→

product

Ausbeute 94.0%

3-Hydroxymethyl-1-(2-mercaptoethyl)pyridinium trifluoromethanesulfonate

Ausbeute 94.0%

Lösungsmittel

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe resulting homogeneous mixture was heated (oil bath) at 50°-70° C. under N2 for 20 h
2. 2
   Extraktionextracted with CH2Cl2 (5×5 mL)
3. 3
   EinengenThe aqueous phase was concentrated in vacuo
4. 4
   WaschenElution with H2O
5. 5
   Sonstigefollowed by evaporation of the relevant fractions
6. 6
   Sonstigegave a pale yellow oil
7. 7
   SonstigeThis material was rechromatographed
8. 8
   Sonstigeto give a nearly colourless oil
9. 9
   TrocknenAfter drying in vacuo (P2O5)

Vorschrift

Trifluoromethanesulfonic acid (1.327 mL, 0.015 mol) was added dropwise to 3-pyridinemethanol (2.91 mL, 0.030 mol), followed by ethylene sulfide (0.89 mL, 0.015 mol). The resulting homogeneous mixture was heated (oil bath) at 50°-70° C. under N2 for 20 h. The reaction mixture was then taken up in H2O (15 mL) and extracted with CH2Cl2 (5×5 mL). The aqueous phase was concentrated in vacuo and then applied to a C18 reverse-phase column. Elution with H2O followed by evaporation of the relevant fractions gave a pale yellow oil. This material was rechromatographed to give a nearly colourless oil. After drying in vacuo (P2O5) this afforded the product (4.50 g, 94%) as a viscous oil. ir (film) νmax : 3450 (s, OH), 2560 (w, SH) cm-1 ; 1Hmr (d6 -acetone)δ: 9.10-8.05 (m, 4H, aromatic), 5.01 (t, J= 5.5 Hz, 2H, N-CH2), 4.93 (s, 2H, --CH2OH), 4.43 (br S, 1H, -OH), 3.43-3.18 (m, 2H, S-CH2), 2.34-2.10 (m, 1H, SH).

Quelle