Borane;tetrahydrofuran → [2-(Methylsulfanyl)pyridin-3-yl]methanol

HRID 7162

Reaction equation

HRID 7162 reaction equation
[CH3:1][S:2][C:3]1(C(O)=O)[CH:8]=[CH:7][CH:6]=[CH:5][NH:4]1.B.C1C[O:16][CH2:15]C1>CO>[CH3:1][S:2][C:3]1[C:8]([CH2:15][OH:16])=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 220185282-(Methylthio)picolinic acid

Product 1

HCID 22018843[2-(Methylsulfanyl)pyridin-3-yl]methanolYield 30.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

To 2-(methylthio)picolinic acid (1.00 g, 5.91 mmol) was added BH3.THF (1.0 M/THF, 15 mL, 15 mmol) and the mixture heated at 80° C. for 24 h. Methanol (30 mL) was carefully added at room temperature and the solution was concentrated in vacuo. Purification of the crude material on silica gel (20% EtOAc/hexanes) gave the title compound as colourless crystals (278 mg, 30%). 1H NMR (CDCl3) □ 1.99 (t, 1H, J=6.0 Hz), 2.61 (s, 3H), 4.70 (d, 2H, J=6.0 Hz), 7.04 (dd, 1H, J=6, 3 Hz), 7.62 (d, 1H, J=6 Hz), 8.40 (d, 1H, J=3 Hz).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customPurification of the crude material on silica gel (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8ca8621f578e448293bc81423498fb78
Source dataset
uspto-grants-2006_08
Patent number
US07084155B2

Linked notes

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