1,1'-Carbonyldiimidazole → Ethyl 3-(5-chloro-2-methoxyphenyl)-3-oxopropanoate

HRID 474328

Reaktionsgleichung

Reaktionsgleichung von HRID 474328
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](C)=[C:6]([CH:10]=1)[C:7]([OH:9])=O.C1N=CN([C:17](N2C=NC=C2)=[O:18])C=1.[C:24]([O:30][CH2:31][CH3:32])(=[O:29])[CH2:25]C([O-])=O.[K+].[Cl-].[Mg+2].[Cl-]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:18][CH3:17])=[C:6]([C:7](=[O:9])[CH2:25][C:24]([O:30][CH2:31][CH3:32])=[O:29])[CH:10]=1

Komponenten

6

Edukt 4

HCID 682631,1'-CarbonyldiimidazoleHCID 820095-Chloro-2-methylbenzoic acidHCID 3446434Potassium ethyl malonateHCID 5360315Magnesium Chloride

Produkt 1

HCID 54012347Ethyl 3-(5-chloro-2-methoxyphenyl)-3-oxopropanoateAusbeute 118 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirring solution of 5-chloro-2-methylbenzoic acid (4.85 g, 28.4 mmol) in tetrahydrofuran (30 mL) was added N,N-carbonyldiimidazole (4.87 g, 30.0 mmol, 1.06 equiv). After 30 minutes, the reaction mixture was added to a suspension of potassium ethyl malonate (11.61 g, 68.22 mmol, 2.40 equiv) and magnesium chloride (3.27 g, 34.3 mmol, 1.21 equiv) in tetrahydrofuran (50 mL). The resultant suspension was heated at 50° C. After hours, the reaction mixture was partitioned between ethyl acetate and water. The organic portion was dried over magnesium sulfate, filtered, and concentrated to provide 8.07 g (118%) of ethyl 3-(5-chloro-2-methoxyphenyl)-3-oxopropanoate which was used without purification. LCMS (ESI) m+H=241.2

Aufarbeitung

  1. waitAfter hours
  2. customthe reaction mixture was partitioned between ethyl acetate and water
  3. dry with materialThe organic portion was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6902af7ba6ec4cafb811af10766cae5d
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637526B2

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