Sodium Hydroxide → 5,5-Dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalene-2-carboxylic acid

HRID 481224

Reaktionsgleichung

Reaktionsgleichung von HRID 481224
[CH3:1][C:2]1([CH3:21])[CH2:11][CH:10]=[C:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:8]2[CH:7]=[C:6]([C:17]([O:19]C)=[O:18])[CH:5]=[CH:4][C:3]1=2.[OH-].[Na+]>CCO.C1COCC1>[CH3:1][C:2]1([CH3:21])[CH2:11][CH:10]=[C:9]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)[C:8]2[CH:7]=[C:6]([C:17]([OH:19])=[O:18])[CH:5]=[CH:4][C:3]1=2

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 10494326Methyl 5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-2-naphthalenecarboxylate2×

Produkt 1

HCID 107081975,5-Dimethyl-5,6-dihydro-8-(2-thienyl)-naphthalene-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
35 °C

Versuchsvorschrift

To a solution of methyl 5,5-dimethyl-5,6-dihydro-8-(2-thienyl)-2-naphthalenecarboxylate (Compound E5, 430.0 mg, 1.44 mmol) in 3.0 mL of EtOH and 3.0 mL THF was added NaOH (240.0 mg, 6.00 mmol; 3.0 mL of a 2N aqueous solution). The resulting solution was warmed to 35° C. for 6 h, cooled to room temperature and quenched with 1M HCl. The mixture was extracted with EtOAc and the combined organic layers washed with H2O and saturated aqueous NaCl before being dried over MgSO4. Removal of the solvents under reduced pressure afforded the title compound as a pale yellow solid.

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customquenched with 1M HCl
  3. extractionThe mixture was extracted with EtOAc
  4. washthe combined organic layers washed with H2O and saturated aqueous NaCl
  5. dry with materialbefore being dried over MgSO4
  6. customRemoval of the solvents under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f8deca54a1974d4d972b5c0a7e1b6e70
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06653483B1

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