4-Formylbenzoic acid → 4-[3-Oxo-3-(7,8-dihydro-5-(2-thienyl)-8,8-dimethyl-2-naphthalenyl)-1-propenyl)-benzoic acid

HRID 481222

Reaktionsgleichung

Reaktionsgleichung von HRID 481222
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16](=[O:18])[CH3:17])=[CH:13][CH:14]=2)[C:9]([CH3:20])([CH3:19])[CH2:8][CH:7]=1.[C:21]([C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1)([OH:23])=[O:22].[OH-].[Na+]>CO>[O:18]=[C:16]([C:12]1[CH:13]=[CH:14][C:15]2[C:6]([C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)=[CH:7][CH2:8][C:9]([CH3:20])([CH3:19])[C:10]=2[CH:11]=1)[CH:17]=[CH:28][C:27]1[CH:30]=[CH:31][C:24]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=1

Komponenten

5

Edukt 3

HCID 120884-Formylbenzoic acidHCID 14798Sodium HydroxideHCID 225715413,4-Dihydro-1-(2-thienyl)-4,4-dimethyl-6-acetylnaphthalene

Produkt 1

HCID 545281504-[3-Oxo-3-(7,8-dihydro-5-(2-thienyl)-8,8-dimethyl-2-naphthalenyl)-1-propenyl)-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 62.6 mg (0.222 mmol) 3,4-dihydro-1-(2-thienyl)-4,4-dimethyl-6-acetylnaphthalene (Compound D33) in 4.0 mL of MeOH were added 33.4 mg (0.222 mmol) of 4-carboxy benzaldehyde, and 240.0 mg (6.00 mmol; 2.0 mL of 3M aqueous NaOH). The resulting solution was stirred at room temperature for 12 h, concentrated under reduced pressure, and the residual oil dissolved in EtOAc. The solution was treated with 10% HCl, and the organic layer washed with H2O, and saturated aqueous NaCl, before being dried over Na2SO4. Removal of the solvents under reduced pressure gave the title compound as a pale green solid after recrystallization from EtOH.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. dissolutionthe residual oil dissolved in EtOAc
  3. additionThe solution was treated with 10% HCl
  4. washthe organic layer washed with H2O, and saturated aqueous NaCl
  5. dry with materialbefore being dried over Na2SO4
  6. customRemoval of the solvents under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-cb528c44caae4848b28f8375daf23af3
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06653483B1

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