Sodium Hydroxide → [1-(1-(p-Bromobenzyl)-5-methoxy-2-methylindol-3-yl)cyclopropyl]acetic acid

HRID 1451535Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1451535
[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([C:18]3([CH2:21][C:22]([O:24]C)=[O:23])[CH2:20][CH2:19]3)=[C:8]2[CH3:26])=[CH:4][CH:3]=1.[OH-].[Na+]>CO.CCOCC.CCCCCC>[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([C:18]3([CH2:21][C:22]([OH:24])=[O:23])[CH2:20][CH2:19]3)=[C:8]2[CH3:26])=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 53800337Methyl [1-(1-(p-bromobenzyl)-5-methoxy-2-methylindol-3-yl)cyclopropyl]acetate

Produkt 1

HCID 19041685[1-(1-(p-Bromobenzyl)-5-methoxy-2-methylindol-3-yl)cyclopropyl]acetic acidAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 21584099Diethylether hexaneLösungsmittel

Versuchsvorschrift

To the methyl ester from Step 7 (1.63 g, 3.68 mmol) in 20 mL of methanol was added 5 mL of 2N NaOH, and the mixture was heated to reflux for 2 h then cooled. The reaction mixture was partitioned between ethyl acetate and 1M HCl. The organic layer was washed with brine, dried over MgSO4 and evaporated to give a solid. This material was swished twice in 15% ether/hexane to provide 1.23 g of the title compound.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h
  3. temperaturethen cooled
  4. customThe reaction mixture was partitioned between ethyl acetate and 1M HCl
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customto give a solid

Quellen und Nachweise

ORD-Eintrag
ord-2cfd5522bbad4582b830604fd9c9f0e7
Quelldatensatz
uspto-grants-1997_02
Patentnummer
US05604253

Notizen zur Reaktion

Wird geladen…