Sodium hydride → 4-(4-(Trifluoromethyl)benzyloxy)pyridine 1-oxide

HRID 930641

Reaktionsgleichung

Reaktionsgleichung von HRID 930641
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.[H-].[Na+].Cl[C:16]1[CH:21]=[CH:20][N+:19]([O-:22])=[CH:18][CH:17]=1>CN(C=O)C.C(Cl)Cl>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:10]=[CH:9][C:6]([CH2:7][O:8][C:16]2[CH:21]=[CH:20][N+:19]([O-:22])=[CH:18][CH:17]=2)=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 676844-(Trifluoromethyl)benzenemethanolHCID 707244-chloropyridine N-oxide

Produkt 1

HCID 686576494-(4-(Trifluoromethyl)benzyloxy)pyridine 1-oxideAusbeute 19,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

4-Trifluoromethylbenzylalcohol (4.2 g, 23 mmol) was dissolved in DMF (20 mL) and NaH (60% weight dispersion in mineral oil, 0.92 g, 23 mmol) was added. After stirring for 30 minutes, 4-chloropyridine-N-oxide (1.5 g, 11.5 mmol) was added and the reaction mixture was heated for 1 h at 120° C. Upon cooling the mixture was diluted with methylene chloride and washed with 5% lithium chloride solution (5×), dried and concentrated. Purification by flash column chromatography (40 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 90% methylene chloride over 30 min at 40 mL/min) provided the title compound (0.6 g, 19%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 8.14 (d, J=7.8 Hz, 2H), 7.68 (d, J=8.1 Hz, 2H), 7.52 (d, J=8.1 Hz, 2H), 6.86 (d, J=7.8 Hz, 2H), 5.15 (s, 2H).

Aufarbeitung

  1. temperatureUpon cooling the mixture
  2. washwashed with 5% lithium chloride solution (5×)
  3. customdried
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (40 g ISCO column
  6. washeluting with methylene chloride

Quellen und Nachweise

ORD-Eintrag
ord-83be219abc464325a3129b22aad7ffa8
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296743B2

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