Benzyl Alcohol → 5-Benzyloxy-2-bromoisonicotinic acid ethyl ester

HRID 1516576Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1516576
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:11]([O:13][C:14](=[O:23])[C:15]1[C:20](F)=[CH:19][N:18]=[C:17]([Br:22])[CH:16]=1)[CH3:12].O>O1CCCC1>[CH2:11]([O:13][C:14](=[O:23])[C:15]1[C:20]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:19][N:18]=[C:17]([Br:22])[CH:16]=1)[CH3:12]

Komponenten

6

Edukt 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 46311464Ethyl 2-bromo-5-fluoroisonicotinate

Produkt 1

HCID 866451665-Benzyloxy-2-bromoisonicotinic acid ethyl esterAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of benzylalcohol (1.5 g) in tetrahydrofuran (30 mL) was added sodium hydride (55%, 0.3 g) under ice cooling, and this mixture was stirred at same temperature for 5 minutes. To this reaction mixture was added a solution of 2-bromo-5-fluoroisonicotinic acid ethyl ester (2.9 g) in tetrahydrofuran (30 mL), and this mixture was stirred at room temperature for 2 hours. This reaction mixture was poured into water, and this mixture was extracted with ethyl acetate. This organic layer was washed with water and brine, dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane) to give the title compound (2.4 g).

Aufarbeitung

  1. stirringthis mixture was stirred at room temperature for 2 hours
  2. extractionthis mixture was extracted with ethyl acetate
  3. washThis organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d065cf9f2b0a4ff5848da959da3199fd
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08227500B2

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