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

HRID 368300ノート

反応式

HRID 368300 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[N:9]1([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[C:23](=[O:27])[CH2:22][CH2:21][CH2:20]3)[CH:13]=[CH:12][N:11]=[CH:10]1.Cl.C([O-])(O)=O.[Na+]>N1CCCCC1.C(O)(=O)C>[N:9]1([CH2:14][CH2:15][O:16][C:17]2[CH:18]=[C:19]3[C:24](=[CH:25][CH:26]=2)[C:23](=[O:27])[C:22](=[CH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[CH2:21][CH2:20]3)[CH:13]=[CH:12][N:11]=[CH:10]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 142732-PyridinecarboxaldehydeHCID 516892Sodium BicarbonateHCID 154869126-(2-Imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one

生成物 1

HCID 545271026-(2-Imidazole-1-yl-ethoxy)-2-pyridin-2-ylmethylene-3,4-dihydro-2H-naphthalen-1-one収率 18.1%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8082Piperidine溶媒

反応条件

温度
130 °C

実験手順

2-Pyridine carboxaldehyde (0.202 g, 1.9 mmol) was added to a mixture of 6-(2-imidazole-1-yl-ethoxy)-3,4-dihydro-2H-naphthalen-1-one (1) (0.322 g, 1.2 mmol) in piperidine:acetic acid (30 μL:24 μL). The reaction mixture was heated in a 130° C. oil bath with efficient stirring for 1.5 hours. After cooling to room temperature, 2 mL of 1N HCl was added and the mixture stirred overnight. The mixture was made neutral with the addition of a saturated solution of NaHCO3 and then extracted into DCM (3×50 mL). The pooled extracts were washed sequentially several times with water, then brine, dried, filtered, and concentrated in vacuo to leave a dark brown oil. Purification by flash chromatography (silica gel, 135 g, 7% MeOH in DCM) afforded 0.075 g of the title compound as a light tan solid.

後処理

  1. temperatureAfter cooling to room temperature
  2. stirringthe mixture stirred overnight
  3. extractionextracted into DCM (3×50 mL)
  4. washThe pooled extracts were washed sequentially several times with water
  5. dry with materialbrine, dried
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto leave a dark brown oil
  9. customPurification by flash chromatography (silica gel, 135 g, 7% MeOH in DCM)

出典と根拠

ORDレコード
ord-e9272fc3d6cf4d829ff1692a50833b89
出典データセット
uspto-grants-2000_10
特許番号
US06133303

反応ノート

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