Methanol → (4-(Pyridin-2-yloxy)benzene)-acetohydroximoyl chloride

HRID 78252Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 78252
CO.[N+:3]([CH2:6][CH2:7][C:8]1[CH:20]=[CH:19][C:11]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:10][CH:9]=1)([O-])=[O:4].C[O-].[Li+].O1CCCC1.C(Cl)[Cl:30]>[Ti](Cl)(Cl)(Cl)Cl.C(OCC)(=O)C>[C:6]([Cl:30])(=[N:3][OH:4])[CH3:7].[N:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[O:12][C:11]1[CH:10]=[CH:9][CH:8]=[CH:20][CH:19]=1

Komponenten

8

Edukt 5

HCID 887MethanolHCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 4177230Lithium methanolateHCID 592552412-(4-(2-Nitro-ethyl)-phenoxy)-pyridine

Produkt 1

HCID 86612460(4-(Pyridin-2-yloxy)benzene)-acetohydroximoyl chlorideAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-76 °C

Versuchsvorschrift

To a methanol solution (30 mL) of 2-(4-(2-nitro-ethyl)-phenoxy)-pyridine (2.0 g, 8.2 mmol) described in Manufacturing Example 209-1-3 was added lithium methoxide (470 mg, 12 mmol), and this mixture was concentrated under a reduced pressure. Toluene was added to the residue, and the solvent was evaporated under a reduced pressure. To a solution of this residue in methylene chloride (40 mL) and tetrahydrofuran (20 mL) was added titanium (IV) tetrachloride (2.3 mL, 21 mmol) while stirring at −76° C. This suspension was stirred for 15 minutes at 0° C., and then for another 20 minutes at room temperature. The mixture was poured into ice water and stirred for 30 minutes. Ethyl acetate was added, and the organic layer was separated, washed with aqueous sodium chloride (one time), dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under a reduced pressure to obtain the title compound (2.1 g, 98%).

Aufarbeitung

  1. concentrationthis mixture was concentrated under a reduced pressure
  2. additionToluene was added to the residue
  3. customthe solvent was evaporated under a reduced pressure
  4. stirringThis suspension was stirred for 15 minutes at 0° C.
  5. stirringstirred for 30 minutes
  6. customthe organic layer was separated
  7. washwashed with aqueous sodium chloride (one time)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under a reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-37c083ec716e4e90b2a664e3bd47815a
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841327B2

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