Water → HCID 54119952, compound

HRID 1291590Notes

Reaction equation

HRID 1291590 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]2[S:9][C:10]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[CH:11][CH:12]=2)=[CH:5][CH:4]=1)=[O:2].O.[C:19](OCC)(=O)[CH3:20]>C1COCC1>[OH:2][CH:1]([C:3]1[S:7][C:6]([C:8]2[S:9][C:10]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)=[CH:11][CH:12]=2)=[CH:5][CH:4]=1)[CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 454742(2,2':5',2''-Terthiophene)-5-carboxaldehyde

Product 1

HCID 54119952HCID 54119952, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3.5 g of 5-formyl-2,2':5',2"-terthiophene was dissolved in 200 ml of anhydrous THF under nitrogen stream. 7.9 ml of ethyl Grignard reagent was dropped in slowly under ice bath temperature and stirred at 0° C. for 1 hour. The reaction mixture was then heated to 70° C. in oil bath for 4 hours. The solution was monitored by thin layer chromatography to determine whether the reaction was completed. 50 ml of water and 300 ml of ethyl acetate were added and the ethyl acetate extract was purified by column chromatography. From the eluate of ethyl acetate/n-hexane (1/9) fraction, yellow solid was obtained and recrystallized to give granulate crystal. The melting point of the product was 89°-90° C. and the yield was about 70%.

Workup

  1. temperatureThe reaction mixture was then heated to 70° C. in oil bath for 4 hours
  2. extractionthe ethyl acetate extract
  3. customwas purified by column chromatography
  4. customFrom the eluate of ethyl acetate/n-hexane (1/9) fraction, yellow solid was obtained
  5. customrecrystallized
  6. customto give granulate crystal
  7. customwas 89°-90° C.

Sources & evidence

ORD record
ord-1894cbc0bb8840f0ac11a4d21a82b5bc
Source dataset
uspto-grants-1998_05
Patent number
US05753692

Reaction notes

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