Dichloromethane → Methyl 2-(4-trifluoromethyl-2-pyridyloxy)propionate

HRID 1160716Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1160716
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([O:9][CH:10]([CH3:14])[C:11]([OH:13])=[O:12])[CH:4]=1.[CH2:17](Cl)Cl>CO.CCCCCC>[F:16][C:2]([F:15])([F:1])[C:3]1[CH:8]=[CH:7][N:6]=[C:5]([O:9][CH:10]([CH3:14])[C:11]([O:13][CH3:17])=[O:12])[CH:4]=1

Komponenten

5

Edukt 2

HCID 6344DichloromethaneHCID 22270370HCID 22270370, Verbindung

Produkt 1

HCID 22270664Methyl 2-(4-trifluoromethyl-2-pyridyloxy)propionate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(4-trifluoromethyl-2-pyridyloxy)propionic acid (Step A, 15 g, 55 mol) in 100 mL CH2Cl2 and 100 mL MeOH at 0° C. was added trimethylsilydiazomethane (2 M solution in hexane) until a yellow color persisted. After stirring at room temperature for 15 min, the reaction mixture was concentrated to dryness, and the residue was purified by flash chromatography on silica gel eluted with 0 to 10% EtOAc in hexane to give methyl 2-(4-trifluoromethyl-2-pyridyloxy)propionate (10 g), which was used immediately for methylation following the procedure described in Reference Example 39, Step B substituting ethyl iodide with methyl iodide. 1H NMR (500 MHz, CD3OD): δ 8.25 (d, 1H), 7.18 (d, 1H), 7.15 (s, 1H), 3.65 (s, 3H), 1.65 (s, 6H).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated to dryness
  2. customthe residue was purified by flash chromatography on silica gel
  3. washeluted with 0 to 10% EtOAc in hexane

Quellen und Nachweise

ORD-Eintrag
ord-9d37507044144abebffe2cb8fa40b3fa
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07816534B2

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