Sodium hydride → 1-[4-(2,2-Diethoxyethoxy)phenyl]cyclopropanecarboxylic acid

HRID 17923

Reaktionsgleichung

Reaktionsgleichung von HRID 17923
C[O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4].[H-].[Na+].[H][H].Br[CH2:20][CH:21]([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24]>CN(C=O)C>[CH2:23]([O:22][CH:21]([O:25][CH2:26][CH3:27])[CH2:20][O:14][C:11]1[CH:12]=[CH:13][C:8]([C:5]2([C:3]([OH:2])=[O:4])[CH2:7][CH2:6]2)=[CH:9][CH:10]=1)[CH3:24]

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 20770793Methyl 1-(4-hydroxyphenyl)cyclopropane-1-carboxylateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 591292871-[4-(2,2-Diethoxyethoxy)phenyl]cyclopropanecarboxylic acidAusbeute 40,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

To a stirred solution of 1-(4-hydroxy-phenyl)-cyclopropanecarboxylic acid methyl ester (15.0 g, 84.3 mmol) in DMF (50 mL) was added sodium hydride (6.7 g, 170 mmol, 60% in mineral oil) at 0° C. After hydrogen evolution ceased, 2-bromo-1,1-diethoxy-ethane (16.5 g, 84.3 mmol) was added dropwise to the reaction mixture. The reaction was stirred at 160° C. for 15 hours. The reaction mixture was poured onto ice (100 g) and extracted with CH2Cl2. The combined organics were dried over Na2SO4. The solvent was evaporated under vacuum to give crude 1-[4-(2,2-diethoxy-ethoxy)-phenyl]-cyclopropanecarboxylic acid (10 g), which was used directly in the next step without purification.

Aufarbeitung

  1. additionThe reaction mixture was poured onto ice (100 g)
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organics were dried over Na2SO4
  4. customThe solvent was evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-387cdd7a236b44f9a254edc37faf6592
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741321B2

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