Borane;tetrahydrofuran → Methyl 2-(5-fluoro-2-(methyloxy)-4-pyridinyl)-5-(hydroxymethyl)benzoate

HRID 404332Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 404332
[F:1][C:2]1[C:3]([C:10]2[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][C:11]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.B.C1COCC1>C1COCC1>[F:1][C:2]1[C:3]([C:10]2[CH:18]=[CH:17][C:13]([CH2:14][OH:15])=[CH:12][C:11]=2[C:19]([O:21][CH3:22])=[O:20])=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 2723981Borane;tetrahydrofuranHCID 574675964-(5-Fluoro-2-(methyloxy)-4-pyridinyl)-3-((methyloxy)carbonyl)benzoic acid

Produkt 1

HCID 57467597Methyl 2-(5-fluoro-2-(methyloxy)-4-pyridinyl)-5-(hydroxymethyl)benzoateAusbeute 105,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To a stirred solution of 4-(5-fluoro-2-methoxypyridin-4-yl)-3-(methoxycarbonyl)benzoic acid T6.2 (0.416 g, 1 mmol) in THF (14 mL) at 0° C. was added borane-THF (3 mL, 3 mmol, 1.0M). The reaction was warmed to 23° C. and stirred for 46 hours. The reaction was then concentrated in vacuo, diluted with 1N HCl and extracted three times with EtOAc. The organic layers were combined, dried over anhydrous MgSO4, and filtered. The organic solvent was removed under reduced pressure, and the product was purified on silica gel (0-40% EtOAc in hexanes) to yield T6.3 as a colorless solid (0.307 g, 77% yield).

Aufarbeitung

  1. concentrationThe reaction was then concentrated in vacuo
  2. additiondiluted with 1N HCl
  3. extractionextracted three times with EtOAc
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe organic solvent was removed under reduced pressure
  7. customthe product was purified on silica gel (0-40% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-43b1815264244558b16c492246cc8fe9
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08748462B2

Notizen zur Reaktion

Wird geladen…