Water → HCID 86667565、化合物

HRID 85273ノート

反応式

HRID 85273 の反応式
[CH2:1]([N:5]([CH2:22][CH2:23][CH2:24][CH3:25])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[S:18][C:17]([CH:19]=[O:20])=[CH:16][CH:15]=2)=[C:8]([OH:21])[CH:7]=1)[CH2:2][CH2:3][CH3:4].[CH2:26]([CH:28]1[O:30][CH2:29]1)Br.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH2:22]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]2[S:18][C:17]([CH:19]=[O:20])=[CH:16][CH:15]=2)=[C:8]([O:21][CH2:26][CH:28]2[CH2:29][O:30]2)[CH:7]=1)[CH2:23][CH2:24][CH3:25]

参加物

8

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 86667563HCID 86667563、化合物

生成物 1

HCID 86667565HCID 86667565、化合物収率 58.5%

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

In 10 ml of acetonitrile were dissolved 390 mg (1.09 mmol) of 5-[2-(4-dibutylamino-2-hydroxyphenyl) vinyl]thiophene-2-carboaldehyde and 0.22 g (1.61 mmol) of epibromohydrin. To this mixture were added 0.3 g (2.17 mmol) of anhydrous potassium carbonate and 40 mg of tetrabutylammonium iodide, and the mixture was stirred with heating at 60° C. for 4 hours. After the reaction mixture was poured into water, extraction with ethyl acetate, washing with a saturated saline solution, drying over anhydrous sodium sulfate, and concentration were performed. The residue was purified by silica gel column chromatography. The oily matter was dissolved in 50 ml of ether and 10 mg of iodine was added thereto. The mixture was stirred for 1 hour. The mixture was washed with a 5% sodium bisulfite solution and then with a saturated saline solution. Drying over anhydrous magnesium sulfate and concentration were performed. The residual liquid was purified by silica gel column chromatography to give 264 mg of a dark reddish brown oily matter (yield: 58.5%).

後処理

  1. washwashing with a saturated saline solution
  2. dry with materialdrying over anhydrous sodium sulfate, and concentration
  3. customThe residue was purified by silica gel column chromatography
  4. dissolutionThe oily matter was dissolved in 50 ml of ether
  5. addition10 mg of iodine was added
  6. stirringThe mixture was stirred for 1 hour
  7. washThe mixture was washed with a 5% sodium bisulfite solution
  8. dry with materialDrying over anhydrous magnesium sulfate and concentration
  9. customThe residual liquid was purified by silica gel column chromatography
  10. customto give 264 mg of a dark reddish brown oily matter (yield: 58.5%)

出典と根拠

ORDレコード
ord-0ada61cf973a40b29e4664dd7207d5d2
出典データセット
uspto-grants-2014_09
特許番号
US08846955B2

反応ノート

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