Tetrahydrofuran → 3-(2-Hydroxyethyl)-1H-indole-2-carboxylic acid

HRID 858278Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 858278
[C:1]1(=[O:14])[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH2:3][O:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.C1C[O:18]CC1>>[OH:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:1]([OH:14])=[O:18]

Komponenten

3

Edukt 2

HCID 8028TetrahydrofuranHCID 3261784,9-dihydro-3H-pyrano[3,4-b]indol-1-one

Produkt 1

HCID 166410173-(2-Hydroxyethyl)-1H-indole-2-carboxylic acid

Versuchsvorschrift

To a solution of 4,9-dihydro-3H-pyrano[3,4-b]indol-1-one (Arch. Pharm., 1987, 320, 1202–1209, 5.225 g, 27.9 mmol) in THF (25 mL) was added deoxygenated 3 N KOH (25 mL). The mixture was stirred at room temperature for 4.5 hours. The reaction mixture was washed with EtOAc, acidified with 1 N HCl, and extracted with EtOAc. The organic extract was dried over MgSO4 and concentrated to give 5.589 g of 3-(2-hydroxyethyl)-1H-indole-2-carboxylic acid as a solid. This material was used for the next reaction without further purification: 1H NMR (DMSO-d6) δ 3.26 (t, J=7.5 Hz, 2H), 3.63 (t, J=7.5 Hz, 2H), 7.08 (t, J=7.5 Hz, 1H), 7.26 (t, J=7.7 Hz, 1H), 7.43 (d, J=8.3 Hz, 1H), 7.69 (d, J=8.1 Hz, 1H). Anal. Calcd. for C11H11NO3.0.1 EtOAc: C., 63.98; H, 5.56; N, 6.54. Found: C, 63.90; H, 5.57; N, 6.46.

Aufarbeitung

  1. customdeoxygenated 3 N KOH (25 mL)
  2. washThe reaction mixture was washed with EtOAc
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-82251ce25f4148beb22d85fd063c2b42
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07148250B2

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