Benzyl Alcohol → 3-Benzyloxy-5-(Trifluoromethyl)Pyridine

HRID 617335

Reaktionsgleichung

Reaktionsgleichung von HRID 617335
Cl[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[H-].[Na+].[CH2:14]([OH:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C=O)C>[CH2:14]([O:21][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

5

Edukt 3

HCID 244Benzyl AlcoholHCID 24758Sodium hydrideHCID 27366983-Chloro-5-(trifluoromethyl)pyridine

Produkt 1

HCID 218518253-Benzyloxy-5-(Trifluoromethyl)Pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 3.63 g (20 mmol) sample of 3-chloro-5-trifluoromethylpyridine dissolved in 15 mL of DMF and cooled to 0° C. was added 960 mg of NaH (60%), 2.07 mL of benzyl alcohol was added slowly. The reaction mixture was stirred for 2 hours at 40° C. The solvent was then evaporated in vacuo and the mixture diluted with chloroform, washed with saturated NaHCO3 and a brine solution. The organic layer was then dried over MgSO4. The resulting crude material was purified by flash chromatography on silica gel to give the title product. MS (DCI/NH3) m/e 154 (M+H)+. 1H NMR (CDCl3, 300 MHz) d: 8.56 (d, J=1.8 Hz, 1H), 8.47 (d, J=0.9 Hz, 1H), 7.51 (dd, J=1, 0.9 Hz, 1H).

Aufarbeitung

  1. additionwas added slowly
  2. customThe solvent was then evaporated in vacuo
  3. additionthe mixture diluted with chloroform
  4. washwashed with saturated NaHCO3
  5. dry with materialThe organic layer was then dried over MgSO4
  6. customThe resulting crude material was purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-5af9cf79592a411eacdd36a2ff679154
Quelldatensatz
uspto-grants-1999_09
Patentnummer
US05948793

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