Water → 5-(4-Acetoxybut-1-ynyl)-2,2'-bithiophene

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

Reactant 4

HCID 962Water

HCID 1049Pyridine

HCID 7918Acetic Anhydride

HCID 54099739HCID 54099739, compound

Product 1

HCID 4403565-(4-Acetoxybut-1-ynyl)-2,2'-bithiophene

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 reproved 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.