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

HRID 280229노트

반응식

HRID 280229 반응식
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

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2a9dd7f796434117aa065e413a387abe
출처 데이터셋
uspto-grants-1986_05
특허 번호
US04588732

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