Borane;tetrahydrofuran → (3-Ethoxypyridin-2-yl)methanol

HRID 747348

Reaktionsgleichung

Reaktionsgleichung von HRID 747348
[CH2:1]([O:3][C:4]1[C:5]([C:10](O)=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2].B.C1COCC1>C1COCC1>[CH2:1]([O:3][C:4]1[C:5]([CH2:10][OH:11])=[N:6][CH:7]=[CH:8][CH:9]=1)[CH3:2]

Komponenten

4

Edukt 2

HCID 2723981Borane;tetrahydrofuranHCID 213332043-Ethoxypyridine-2-carboxylic acid

Produkt 1

HCID 22018715(3-Ethoxypyridin-2-yl)methanolAusbeute 124,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-ethoxypicolinic acid (0.202 g, 1.21 mmol) in dry THF (1 mL) was added BH3.THF (1.0 M in THF, 5.0 mL, 5.0 mmol) and the reaction mixture stirred at room temperature for 2.5 hours. The mixture was then quenched with methanol (20 mL), stirred at reflux for 4 hours and concentrated under reduced pressure. The resultant crude product was dissolved in methanol (3×15 mL) and concentrated to give the desired crude alcohol (0.231 g) as an orange solid. 1H NMR (CDCl3): δ 1.46 (t, 3H, J=7.0 Hz), 4.07 (q, 2H, J=7.0 Hz), 4.74 (s, 2H), 7.09-7.20 (m, 2H), 8.14 (d, 1H, J=4.5 Hz).

Aufarbeitung

  1. customThe mixture was then quenched with methanol (20 mL)
  2. stirringstirred
  3. temperatureat reflux for 4 hours
  4. concentrationconcentrated under reduced pressure
  5. dissolutionThe resultant crude product was dissolved in methanol (3×15 mL)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-088ceb97789d451abbd7995fd00938c6
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396840B2

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