Sodium Hydroxide → 1-(4-((3-(Azido(phenyl)methyl)phenoxy)methyl)phenyl)cyclopropanecarboxylic acid

HRID 332684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 332684
[N:1]([CH:4]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:5]1[CH:6]=[C:7]([CH:23]=[CH:24][CH:25]=1)[O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:19]([O:21]C)=[O:20])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)=[N+:2]=[N-:3].[OH-].[Na+]>CO.O1CCCC1>[N:1]([CH:4]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:5]1[CH:6]=[C:7]([CH:23]=[CH:24][CH:25]=1)[O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]2([C:19]([OH:21])=[O:20])[CH2:18][CH2:17]2)=[CH:14][CH:15]=1)=[N+:2]=[N-:3]

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 71093144Methyl 1-(4-((3-(azido(phenyl)methyl)phenoxy)methyl)-phenyl)cyclopropanecarboxylate

Produkt 1

HCID 710930671-(4-((3-(Azido(phenyl)methyl)phenoxy)methyl)phenyl)cyclopropanecarboxylic acidAusbeute 100,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a stirred solution of methyl 1-(4-((3-(azido(phenyl)methyl)phenoxy)methyl)-phenyl)cyclopropanecarboxylate (0.569 g, 1.375 mmol) in methanol (12.9 mL) and tetrahydrofuran (5.1 mL), was added 2M aqueous sodium hydroxide (12.9 mL). The reaction was stirred at 50° C. for 3 hours 30 minutes and then at room temperature for 16 hours. The reaction mixture was concentrated under reduced pressure, and the pH was adjusted to pH4 using 2M aqueous hydrochloric acid with stirring. The mixture was extracted with dichloromethane (×3), and the combined organic extracts washed with brine, dried (magnesium sulfate), filtered, and concentrated under reduced pressure to afford the title compound (0.552 g, quantitative yield). The material was used directly in the next step with no further purification

Aufarbeitung

  1. waitat room temperature for 16 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. stirringwith stirring
  4. extractionThe mixture was extracted with dichloromethane (×3)
  5. washthe combined organic extracts washed with brine
  6. dry with materialdried (magnesium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-3b504a6e121b4b11b8ebfb6ae935e1e1
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877774B2

Notizen zur Reaktion

Wird geladen…