Water → 3-Butyn-1-ol, 4-(5-(2-thienyl)-2-thienyl)-, acetate

HRID 1901767Notes

Reaction equation

HRID 1901767 reaction equation
OCCC#C[C:6]1[CH:7]=[C:8]([C:11]2[S:12][CH:13]=[CH:14][CH:15]=2)[S:9][CH:10]=1.[C:16]([O:19][C:20](=[O:22])[CH3:21])(=O)[CH3:17].O.N1C=CC=[CH:26][CH:25]=1>>[C:20]([O:19][CH2:16][CH2:17][C:25]#[C:26][C:13]1[S:12][C:11]([C:8]2[S:9][CH:10]=[CH:6][CH:7]=2)=[CH:15][CH:14]=1)(=[O:22])[CH3:21]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 54099739HCID 54099739, compound

Product 1

HCID 4403563-Butyn-1-ol, 4-(5-(2-thienyl)-2-thienyl)-, acetate

Procedure

4-(Hydroxy-1-butynyl)-2,2'-bithiophene (1.23 g) was dissolved in pyridine (6 ml ). Acetic anhydride (1 ml ) was added at room temperature, stirred for few minutes and further kept overnight. Water (20 ml) was added oily product was then extracted with 30 ml of ethyl acetate. The extract was washed with 10 ml of HCl (1N) for 3 times, 10 ml of water once and 10 ml of diluted KHCO3 solution once. Ethyl acetate was then removed under reduced pressure. The residual solid was purified by silica gel column chromatography, eluted with ethyl acetate/n-hexane (1/19). Light yellowish oily product (1.7 g) was obtained after removal of the solvent.

Workup

  1. extractionwas then extracted with 30 ml of ethyl acetate
  2. washThe extract was washed with 10 ml of HCl (1N) for 3 times, 10 ml of water once
  3. customEthyl acetate was then removed under reduced pressure
  4. customThe residual solid was purified by silica gel column chromatography
  5. washeluted with ethyl acetate/n-hexane (1/19)

Sources & evidence

ORD record
ord-6d591e810bb94915ba0822497bfc1e9e
Source dataset
uspto-grants-1996_11
Patent number
US05578636

Reaction notes

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