3-Pyridinemethanol → HCID 20159236, compound

HRID 1583512Notes

Reaction equation

HRID 1583512 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3]([OH:6])(=[O:5])=[O:4].[N:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][OH:16])[CH:10]=1.[CH2:17]1[S:19][CH2:18]1>O>[F:1][C:2]([F:8])([F:7])[S:3]([O-:6])(=[O:5])=[O:4].[OH:16][CH2:15][C:11]1[CH:10]=[N+:9]([CH2:17][CH2:18][SH:19])[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 75103-PyridinemethanolHCID 9865ThiiraneHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 20159236HCID 20159236, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  1. temperatureThe resulting homogeneous mixture was heated (oil bath) at 50°-70° C. under N2 for 20 h
  2. extractionextracted with CH2Cl2 (5×5 mL)
  3. concentrationThe aqueous phase was concentrated in vacuo
  4. washElution with H2O
  5. customfollowed by evaporation of the relevant fractions
  6. customgave a pale yellow oil
  7. customThis material was rechromatographed
  8. customto give a nearly colourless oil
  9. dry with materialAfter drying in vacuo (P2O5)

Sources & evidence

ORD record
ord-fed7c253f2b343c7893534fb1067e1e9
Source dataset
uspto-grants-1985_11
Patent number
US04552696

Reaction notes

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