Cyclopropanecarboxylic acid, 2-(3-methoxyphenyl)-, ethyl ester → 2-(3-Methoxyphenyl)cyclopropane-1-carboxylic acid

HRID 1994102

Reaktionsgleichung

Reaktionsgleichung von HRID 1994102
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:11][CH:10]2[C:12]([O:14]CC)=[O:13])[CH:6]=[CH:7][CH:8]=1>[OH-].[Na+].CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:11][CH:10]2[C:12]([OH:14])=[O:13])[CH:6]=[CH:7][CH:8]=1

Komponenten

4

Edukt 1

HCID 19358490Cyclopropanecarboxylic acid, 2-(3-methoxyphenyl)-, ethyl ester

Produkt 1

HCID 139722332-(3-Methoxyphenyl)cyclopropane-1-carboxylic acidAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A solution of ethyl 2-(3-methoxyphenyl)cyclopropanecarboxylate (1.63 g, 7.4 mmol) in 3N NaOH (35 mL) and MeOH (35 mL) was heated at 60° C. for 1 h. After cooling to rt, the reaction mixture was concentrated. The residue was dissolved in 1N HCl and extracted with DCM. The organic solutions were dried over Na2SO4, filtered, and concentrated to give the desired product (1.23 g, 87%) which was used without further fication. The cis and trans isomers were separated at a later stage of analog synthesis. LCMS: (FA) ES− 191.3 (M+1).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in 1N HCl
  3. extractionextracted with DCM
  4. dry with materialThe organic solutions were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-41cfcb53f06548289bd2b47e243398fd
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652041B2

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