Potassium Carbonate → 4-Methoxy-3-(2-methylbenzoxazol-5-yl)benzenecarboxaldehyde

HRID 1072228

Reaktionsgleichung

Reaktionsgleichung von HRID 1072228
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7](B(O)O)[CH:8]=1)=[O:2].[CH3:14][C:15]1[O:16][C:17]2[CH:23]=[CH:22][C:21](Br)=[CH:20][C:18]=2[N:19]=1.C([O-])([O-])=O.[K+].[K+]>C(O)C.C1(C)C=CC=CC=1>[CH3:13][O:12][C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:8][C:7]=1[C:21]1[CH:22]=[CH:23][C:17]2[O:16][C:15]([CH3:14])=[N:19][C:18]=2[CH:20]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 27343675-Formyl-2-methoxyphenylboronic acidHCID 101045995-Bromo-2-methyl-1,3-benzoxazole

Produkt 1

HCID 223915884-Methoxy-3-(2-methylbenzoxazol-5-yl)benzenecarboxaldehydeAusbeute 89,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 5-formyl-2-methoxybenzeneboronic acid (1 g, 5.6 mmol), 2-methyl-5-bromobenzoxazole (1 g, 4.72 mmol) and K2CO3 (1.63 g, 11.8 mmol) in ethanol (20 mL) and toluene (40 mL) was degassed prior to addition of Pd(Ph3)4 (55 mg, 0.047 mmol). The mixture was refluxed for 20 hours then cooled and filtered through diatomaceous earth. The filtrate was concentrated in vacuo, extracted with ethyl acetate, washed with water and the organic layer dried over sodium sulphate. The crude was purified by column chromatography (heptane/ethyl acetate 7/3 to 6/4) to give 1.13 g of title compound.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 20 hours
  2. temperaturethen cooled
  3. filtrationfiltered through diatomaceous earth
  4. concentrationThe filtrate was concentrated in vacuo
  5. extractionextracted with ethyl acetate
  6. washwashed with water
  7. dry with materialthe organic layer dried over sodium sulphate
  8. customThe crude was purified by column chromatography (heptane/ethyl acetate 7/3 to 6/4)

Quellen und Nachweise

ORD-Eintrag
ord-aa60f609c0394026adfd3b91ea13627b
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908935B2

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