4-Hydroxybenzaldehyde → 5-[2-(p-Hydroxyphenyl)ethen-1-yl]imidazo[1,5-a]pyridine
Reaction equation
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]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
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.
Workup
- additionis added
- temperatureis then refluxed for 1 hour
- temperaturecooled
- washThe aqueous layer is washed with ethyl acetate
- extractionextracted with ethyl acetate
- dry with materialThe organic phase is dried over sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-2a9dd7f796434117aa065e413a387abe
- Source dataset
- uspto-grants-1986_05
- Patent number
- US04588732
Reaction notes
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