4-Pyridinecarboxaldehyde → 6-(2-Imidazole-1-yl-ethoxy)-2-pyridin-4-ylmethylene-3,4-dihydro-2H-naphthalen-1-one

HRID 368302노트

반응식

HRID 368302 반응식
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[CH2:14][CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=[CH:2]1.[N:20]1[CH:25]=[CH:24][C:23]([CH:26]=O)=[CH:22][CH:21]=1>[OH-].[K+].O>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[C:14](=[CH:26][C:23]2[CH:24]=[CH:25][N:20]=[CH:21][CH:22]=2)[CH2:13][CH2:12]3)[CH:5]=[CH:4][N:3]=[CH:2]1

참가 물질

5

반응물 2

HCID 133894-PyridinecarboxaldehydeHCID 154869126-(2-Imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

생성물 1

HCID 541563396-(2-Imidazole-1-yl-ethoxy)-2-pyridin-4-ylmethylene-3,4-dihydro-2H-naphthalen-1-one수율 21.7%

시약·촉매·용매 2

HCID 962Water용매HCID 14797Potassium Hydroxide용매

실험 절차

6-(2-Imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (0.50 g, 1.95 mmol) was reacted with 4-pyridinecarboxaldehyde (0.248 g, 2.3 mmol) in 2.5 mL of 4% KOH for 8 hours at room temperature. The reaction was diluted with water, the resulting mixture was filtered, and the filtrate was extracted into EtOAc. The combined extracts were evaporated to dryness, and the resulting yellow solid was purified twice by flash chromatography (silica gel, 120 g, 9% MeOH in DCM) to afford 0.146 g of a yellow oil which crystallized on standing. Recrystallization from minimal iPrOH afforded the title compound as a light yellow powder (0.041 g, 6%), mp 128.5-129° C.; CI-MS mi/e 345 (M+), 346 (M+ +1);

후처리

  1. filtrationthe resulting mixture was filtered
  2. extractionthe filtrate was extracted into EtOAc
  3. customThe combined extracts were evaporated to dryness
  4. customthe resulting yellow solid was purified twice by flash chromatography (silica gel, 120 g, 9% MeOH in DCM)

출처 및 근거

ORD 기록
ord-43aa44ca69be463a86d8eb5736337516
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06133303

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