Water → HCID 86667565, compound

HRID 85273Notes

Reaction equation

HRID 85273 reaction equation
[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]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18430EpibromohydrinHCID 86667563HCID 86667563, compound

Product 1

HCID 86667565HCID 86667565, compoundYield 58.5%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

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%).

Workup

  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%)

Sources & evidence

ORD record
ord-0ada61cf973a40b29e4664dd7207d5d2
Source dataset
uspto-grants-2014_09
Patent number
US08846955B2

Reaction notes

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