Pyridine → HCID 18920454, compound

HRID 1599508Notes

Reaction equation

HRID 1599508 reaction equation
[OH:1][CH2:2][C:3]1[S:7][C:6]([C:8]2[S:9][C:10]([CH:13]=[O:14])=[CH:11][CH:12]=2)=[CH:5][CH:4]=1.N1C=CC=CC=1.[C:21](OC(=O)C)(=[O:23])[CH3:22].C(OCC)(=O)C>O>[C:21]([O:1][CH2:2][C:3]1[S:7][C:6]([C:8]2[S:9][C:10]([CH:13]=[O:14])=[CH:11][CH:12]=2)=[CH:5][CH:4]=1)(=[O:23])[CH3:22]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 15818144HCID 15818144, compound

Product 1

HCID 18920454HCID 18920454, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Hydroxymethyl-5'-formyl-2,2'-bithiophene (0.2 g) and pyridine (1 ml) were mixed together. Acetic anhydride (1 ml) was added slowly into the mixture with stirring. Ethyl acetate (200 ml) and water (50 ml) were added 2 hours later. The ethyl acetate layer was washed with weak base, weak acid and water. The product was concentrated and purified by column chromatography, eluted with ethyl acetate/n-hexane (1/9). Light yellowish crystals were obtained. The melting point of the crystal was 89°-91° C. The yield was 95%.

Workup

  1. washThe ethyl acetate layer was washed with weak base, weak acid and water
  2. concentrationThe product was concentrated
  3. custompurified by column chromatography
  4. washeluted with ethyl acetate/n-hexane (1/9)
  5. customLight yellowish crystals were obtained
  6. customwas 89°-91° C

Sources & evidence

ORD record
ord-59ebbd3f308345038d938e902e3683fe
Source dataset
uspto-grants-1998_04
Patent number
US05741811

Reaction notes

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