4-Hydroxybenzaldehyde → 5-[2-(p-Hydroxyphenyl)ethen-1-yl]imidazo[1,5-a]pyridine

HRID 280229Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 280229
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl[CH2:21][C:22]1[N:27]2[CH:28]=[N:29][CH:30]=[C:26]2[CH:25]=[CH:24][CH:23]=1.[H-].[Na+].[OH:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=O)=[CH:36][CH:35]=1.S(=O)(=O)(O)O>O1CCCC1>[OH:33][C:34]1[CH:41]=[CH:40][C:37]([CH:38]=[CH:21][C:22]2[N:27]3[CH:28]=[N:29][CH:30]=[C:26]3[CH:25]=[CH:24][CH:23]=2)=[CH:36][CH:35]=1

Komponenten

7

Edukt 5

HCID 1264-HydroxybenzaldehydeHCID 1118Sulfuric AcidHCID 11776TriphenylphosphineHCID 24758Sodium hydrideHCID 233218555-(Chloromethyl)imidazo[1,5-a]pyridine

Produkt 1

HCID 540585275-[2-(p-Hydroxyphenyl)ethen-1-yl]imidazo[1,5-a]pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Imidazo[1,5-a]pyridine-5-methyltriphenylphosphonium chloride (4.29 g), which is prepared from equimolar quantities of triphenylphosphine and 5-chloromethylimidazo[1,5-a]pyridine, is added to slurry of sodium hydride (0.5 g, 50% mineral oil dispersion) in 100 ml of dry tetrahydrofuran at 0° under nitrogen. After 1 hour at 0° a solution of p-hydroxybenzaldehyde (0.61 g) in 15 ml of dry tetrahydrofuran is added. The reaction is allowed to warm to room temperature, is then refluxed for 1 hour, cooled and acidified with dilute sulfuric acid. The aqueous layer is washed with ethyl acetate, adjusted to pH=7 with 50% sodium hydroxide and extracted with ethyl acetate. The organic phase is dried over sodium sulfate and evaporated to yield 5-[2-(p-hydroxyphenyl)-ethen-1-yl]-imidazo[1,5-a]pyridine.

Aufarbeitung

  1. additionis added
  2. temperatureis then refluxed for 1 hour
  3. temperaturecooled
  4. washThe aqueous layer is washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic phase is dried over sodium sulfate
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2a9dd7f796434117aa065e413a387abe
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04588732

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