Lithium Hydroxide → 4-[2,2-Dimethyl-4-(5-methyl-thiophen-2-yl)-2H-benzo[g]chromen-7-yl]-benzoic acid

HRID 2288315

Reaktionsgleichung

Reaktionsgleichung von HRID 2288315
C([O:3][C:4](=[O:33])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[CH:13][C:14]3[CH:23]=[C:22]4[C:17]([C:18]([C:26]5[S:27][C:28]([CH3:31])=[CH:29][CH:30]=5)=[CH:19][C:20]([CH3:25])([CH3:24])[O:21]4)=[CH:16][C:15]=3[CH:32]=2)=[CH:7][CH:6]=1)C.[Li+].[OH-]>CO.C1COCC1.O>[CH3:24][C:20]1([CH3:25])[CH:19]=[C:18]([C:26]2[S:27][C:28]([CH3:31])=[CH:29][CH:30]=2)[C:17]2[C:22](=[CH:23][C:14]3[CH:13]=[CH:12][C:11]([C:8]4[CH:9]=[CH:10][C:5]([C:4]([OH:33])=[O:3])=[CH:6][CH:7]=4)=[CH:32][C:15]=3[CH:16]=2)[O:21]1

Komponenten

6

Edukt 2

HCID 3939Lithium HydroxideHCID 15887284Ethyl4-[2,2-dimethyl-4-(5-methyl-thien-2-yl)-benzo[1,2-g]-chrom-3-en-7-yl]benzoate2×

Produkt 1

HCID 98453824-[2,2-Dimethyl-4-(5-methyl-thiophen-2-yl)-2H-benzo[g]chromen-7-yl]-benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of ethyl-4-[2,2-dimethyl-4-(5-methyl-thien-2-yl)-benzo[1,2-g]-chrom-3-en-7-yl]benzoate (Compound 11, 18 mg, 0.03 mmol) in methanol (0.5 mL) and THF (1 mL), was added LiOH in water (1M solution, 0.3 mL). The reaction mixture was stirred for 20 hours, the solvent was removed under reduced pressure, the residue dissolved in water (5 mL), washed with ether (10 mL) and the aqueous layer was acidified to PH 5. The aqueous layer was extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with brine, dried, and the solvent was removed under reduced pressure to afford the title compound as a pale yellow solid.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. dissolutionthe residue dissolved in water (5 mL)
  3. washwashed with ether (10 mL)
  4. extractionThe aqueous layer was extracted with ethyl acetate (3×20 mL)
  5. washThe combined organic layers were washed with brine
  6. customdried
  7. customthe solvent was removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ad41243b5cfb452aaa8cf97d3786b542
Quelldatensatz
uspto-grants-2000_07
Patentnummer
US06087505

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