Bromoform → 2-Methoxy-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetic acid

HRID 512606

Reaktionsgleichung

Reaktionsgleichung von HRID 512606
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=2)=[N:4][N:3]=1.[OH-:15].[K+].[CH:17](Br)(Br)Br.[OH-:21].[K+].[CH3:23][OH:24]>CO.O1CCOCC1>[CH3:17][O:15][CH:11]([C:10]1[CH:13]=[CH:14][C:7]([C:5]2[O:6][C:2]([CH3:1])=[N:3][N:4]=2)=[CH:8][CH:9]=1)[C:23]([OH:24])=[O:21]

Komponenten

7

Edukt 4

HCID 5558BromoformHCID 14797Potassium HydroxideHCID 106552074-(5-Methyl-1,3,4-oxadiazol-2-yl)benzaldehydeHCID 23689386Potassium hydroxide methanol

Produkt 1

HCID 584320102-Methoxy-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 4-(5-methyl-1,3,4-oxadiazol-2-yl)benzaldehyde (5.12 g, 27.2 mmol) in anhydrous MeOH (27 mL) and anhydrous dioxane (27 mL) at −15 to −10° C. (bath temperature) was added several drops of a solution of KOH (7.6 g, 135.4 mmol) in MeOH (27 mL). Bromoform (3 mL, 34.4 mmol) was added, then the remaining KOH/MeOH solution was added over a period of 20 min. The mixture was stirred for 1 hr and the cold bath was removed. After stirring for 30 min, the reaction was put over an ice bath and allowed to warm slowly to room temperature overnight then concentrated to dryness. After dissolving in a minimum amount of H2O, the residue was acidified to pH 1 with 6 M HCl. The aqueous mixture was extracted with EtOAc several times with the addition of brine to the aqueous layer during extraction. The combined organics were washed with brine, dried over Na2SO4 and concentrated in vacuo to give 2-methoxy-2-(4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)acetic acid as a semisolid (6.8 g, quantitative yield). The product was used without further purification.

Aufarbeitung

  1. customthe cold bath was removed
  2. stirringAfter stirring for 30 min
  3. customthe reaction was put over an ice bath
  4. concentrationthen concentrated to dryness
  5. dissolutionAfter dissolving in a minimum amount of H2O
  6. extractionThe aqueous mixture was extracted with EtOAc several times with the addition of brine to the aqueous layer during extraction
  7. washThe combined organics were washed with brine
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-823ea4ce97234d80addc1b8a3e9d612f
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09102643B2

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