Methanol → 4-[1 (5-Methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoic acid

HRID 2611

Reaktionsgleichung

Reaktionsgleichung von HRID 2611
[CH3:1][C:2]1[S:6][C:5]([C:7]2[C:20]3[C:11](=[CH:12][C:13]4[C:18]([CH:19]=3)=[C:17]([C:21]3[CH:31]=[CH:30][C:24]([C:25]([O:27]CC)=[O:26])=[CH:23][CH:22]=3)[CH:16]=[CH:15][CH:14]=4)[C:10]([CH3:33])([CH3:32])[CH2:9][CH:8]=2)=[CH:4][CH:3]=1.CO.[Li+].[OH-].O>C1COCC1>[CH3:1][C:2]1[S:6][C:5]([C:7]2[C:20]3[C:11](=[CH:12][C:13]4[C:18]([CH:19]=3)=[C:17]([C:21]3[CH:22]=[CH:23][C:24]([C:25]([OH:27])=[O:26])=[CH:30][CH:31]=3)[CH:16]=[CH:15][CH:14]=4)[C:10]([CH3:33])([CH3:32])[CH2:9][CH:8]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 962WaterHCID 3939Lithium HydroxideHCID 18620054Ethyl 4-[1-(5-methyl-thien-2-yl)-3,4-dihydro 4,4-dimethyl-anthracen-8-yl]-benzoate2×

Produkt 1

HCID 186200524-[1 (5-Methyl-thien-2-yl)3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of ethyl 4-[1-(5-methyl-thien-2-yl)-3,4-dihydro-4,4-dimethyl-anthracen-8-yl]-benzoate (Compound 3, 33 mg, 0.07 mmol), in THF (2 mL), MeOH (2 mL), was added aqueous LiOH (1M solution, 0.2 mL, 0.2 mmol). After 16 hours, water (2 mL) was added to the reaction mixture, about 50% of the organic solvents were removed by distillation, and the mixture was further diluted the mixture with water (5 mL). The reaction mixture was washed with ether (10 mL) and the aqueous layer was acidified to pH 4 and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed water (5 mL), brine (10 mL), dried with MgSO4 and the solvent was removed by distillation. The product was recrystallized from acetone to obtain the title compound as a white solid.

Aufarbeitung

  1. customwere removed by distillation
  2. additionthe mixture was further diluted the mixture with water (5 mL)
  3. washThe reaction mixture was washed with ether (10 mL)
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. washThe combined organic layers were washed water (5 mL), brine (10 mL)
  6. dry with materialdried with MgSO4
  7. customthe solvent was removed by distillation
  8. customThe product was recrystallized from acetone

Quellen und Nachweise

ORD-Eintrag
ord-84ef26d1ad4b4ac3984632c87edd127d
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728846

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