Hydrochloric Acid → 3-Ethynyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid

HRID 2053764Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2053764
[N:1]1([C:6]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([O:14]C)=[O:13])=[CH:10][C:9]=2[C:18]#[C:19][Si](C)(C)C)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[K+].Cl>CO.O>[C:18]([C:9]1[CH:10]=[C:11]([CH:16]=[CH:17][C:8]=1[C:6]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:7])[C:12]([OH:14])=[O:13])#[CH:19]

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 69309966Methyl 4-(pyrrolidin-1-ylcarbonyl)-3-(2-trimethylsilylethynyl)benzoate

Produkt 1

HCID 859770553-Ethynyl-4-(pyrrolidin-1-ylcarbonyl)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

7.70 g (23.4 mmol) of methyl 4-(pyrrolidin-1-ylcarbonyl)-3-(2-trimethylsilylethynyl)benzoate is dissolved in 30 mL of methanol, combined with 46.7 mL (93.4 mmol) 2 molar potassium hydroxide solution, and refluxed for 2 hours. After the elimination of volatile constituents in vacuo, the residue is diluted with demineralized water and acidified with 2 molar hydrochloric acid solution. The aqueous phase is extracted three times with ethyl acetate, the combined organic phases are dried over sodium sulfate, and then the solvent is eliminated in vacuo. Yield: 3.14 g (55%); Rf value: 0.59 (silica gel; dichloromethane/ethanol=4:1); C14H13NO3 (243.27); mass spectrum: (M+H)+=244.

Aufarbeitung

  1. temperaturerefluxed for 2 hours
  2. extractionThe aqueous phase is extracted three times with ethyl acetate
  3. dry with materialthe combined organic phases are dried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-9e667978302d4e51bd4f9949ab87f864
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326791B2

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