Sodium Hydroxide → [2-Phenyl-5-(2-phenyl-1H-indole-6-carbonyl)thiophene-3-yl]acetic acid

HRID 453613Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 453613
C[O:2][C:3](=[O:33])[CH2:4][C:5]1[CH:9]=[C:8]([C:10]([C:12]2[CH:20]=[C:19]3[C:15]([CH:16]=[C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)[NH:18]3)=[CH:14][CH:13]=2)=[O:11])[S:7][C:6]=1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[OH-].[Na+]>CO.C1COCC1>[C:27]1([C:6]2[S:7][C:8]([C:10]([C:12]3[CH:20]=[C:19]4[C:15]([CH:16]=[C:17]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[NH:18]4)=[CH:14][CH:13]=3)=[O:11])=[CH:9][C:5]=2[CH2:4][C:3]([OH:33])=[O:2])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 86646414[2-Phenyl-5-(2-phenyl-1H-indole-6-carbonyl)thiophene-3-yl]acetic acid methyl ester

Produkt 1

HCID 25221754[2-Phenyl-5-(2-phenyl-1H-indole-6-carbonyl)thiophene-3-yl]acetic acidAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 0.44 g (0.97 mmol) of 23 in 7 mL of MeOH and 7 mL of THF was added 1.5 mL (1.5 mmol) of 1 N NaOH solution. The resulting solution was stirred at room temperature for 4 h. The solvent was removed in vacuo, and the residue was diluted with 10 mL of H2O, acidified to pH˜3 with 1N HCl, and extracted with 30 mL of EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/Hex 1:1) to afford 0.36 g (87%) of 8: mp 238-240° C.; 1H NMR (400 MHz, DMSO-d6) δ 12.5 (brs, 1H), 12.04 (s, 1H), 8.00 (s, 1H), 7.93 (d, J=7.4 Hz, 2H), 7.80 (s, 1H), 7.70 (d, J=8.2 Hz, 1H), 7.59-7.48 (m, 9H), 7.38 (t, J=7.1 Hz, 1H), 7.07 (d, J=1.2 Hz, 1H), 3.69 (s, 2H); 13C NMR (100 MHz, CDCl3) δ 186.6, 172.0, 147.4, 141.6, 141.0, 136.3, 132.6, 132.2, 131.9, 131.4, 130.4, 129.2, 129.1, 128.8, 128.3, 125.6, 125.4, 120.5, 99.3, 34.1; IR (KBr) cm−1 3417, 3054, 1713, 1596.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. additionthe residue was diluted with 10 mL of H2O
  3. extractionextracted with 30 mL of EtOAc
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (EtOAc/Hex 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-4ccc19b4f4b84f3684631d8c2bdec399
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08492428B2

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