Water → Methyl 5-chloro-2-phenylpentanoate

HRID 2235793Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2235793
[C:1]1([CH2:7][C:8]([O:10][CH3:11])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[Cl:14][CH2:15][CH2:16][CH2:17]I.O>CN(C=O)C.C(OCC)(=O)C>[Cl:14][CH2:15][CH2:16][CH2:17][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([O:10][CH3:11])=[O:9]

Komponenten

7

Edukt 4

HCID 962WaterHCID 7559Methyl phenylacetateHCID 24758Sodium hydrideHCID 813631-Chloro-3-iodopropane

Produkt 1

HCID 67067286Methyl 5-chloro-2-phenylpentanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittel3×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of methyl phenylacetate (2.0 g) in DMF (5 mL) was added to a solution of sodium hydride (containing mineral oil at 40%, 590 mg) in DMF (20 mL) under ice-cooling. The reaction solution was stirred for 10 minutes, further stirred at room temperature for 30 minutes and then ice-cooled again. A solution of 1-chloro-3-iodopropane (2.99 g) in DMF (5 mL) was added to the reaction mixture, and the reaction solution was stirred at room temperature overnight. Water and ethyl acetate were added to the reaction mixture, and the organic layer was separated. The resulting organic layer washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure to obtain a crude product of methyl 5-chloro-2-phenylpentanoate. Hydrazine monohydrate (8 mL) was added to a solution of the resulting crude methyl 5-chloro-2-phenylpentanoate (3.279 g) in ethanol (20 mL), and the reaction solution was stirred at room temperature overnight. The reaction solution was concentrated under reduced pressure. Saturated sodium bicarbonate water and ethyl acetate and were added to the residue, and the organic layer was separated. The resulting organic layer washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (elution solvent: heptane-ethyl acetate system) to obtain 730 mg of the title compound. The property values of the compound are as follows.

Aufarbeitung

  1. temperaturecooling
  2. stirringfurther stirred at room temperature for 30 minutes
  3. temperatureice-cooled again
  4. stirringthe reaction solution was stirred at room temperature overnight
  5. customthe organic layer was separated
  6. washThe resulting organic layer washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-0159ca7883e64242a5ddb40c92412f9b
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07713993B2

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