Methyl iodide → Methyl 2-(3-chloro-4-cyanophenyl)propanoate

HRID 1428744

Reaktionsgleichung

Reaktionsgleichung von HRID 1428744
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[H-].[Na+].I[CH3:18]>CN(C)C=O.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([CH3:18])[C:11]([O:13][CH3:14])=[O:12])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Komponenten

7

Edukt 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 3564186Methyl 2-(3-chloro-4-cyanophenyl)acetate

Produkt 1

HCID 70855557Methyl 2-(3-chloro-4-cyanophenyl)propanoateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of methyl 2-(3-chloro-4-cyanophenyl)acetate (931 mg, 4.441 mmol) in dimethylformamide were added 60% sodium hydride (178 mg, 4.441 mmol) and iodomethane (0.3 mL, 4.441 mmol) at 0° C. The reaction mixture was stirred for 1 h at 0° C., then diluted with water. The residue dissolved in ethyl acetate and washed with water and brine. The organic layer was dried over magnesium sulfate and filtered. The filtrate removed in vacuo. The crude was purified by column chromatography to give methyl 2-(3-chloro-4-cyanophenyl)propanoate (642 mg, 65%).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThe filtrate removed in vacuo
  5. customThe crude was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a36f6823ed184d408c51f0b8ce0befca
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937092B2

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