Propargyl alcohol → 5-(3-Hydroxy-1-propynyl)-2,2'-bithiophene

To the mixture of 48 mg (0.86 mmole) of propargyl alcohol, 1 ml of benzene, 0.1 g of 5-iodo-2,2'-bithiophene (0.34 mmole) was added 0.25 g of CuI, 0.05 g of benzyltriethylammonium chloride and 0.1 g of Pd(PPh3)4. To the solution, 3 ml of NaOH solution (2.5 N) was added at room temperature and stirred for 2 hours. 4 ml of NH4Cl solution was then added. The reaction solution was extracted with 50 ml of ethyl acetate. The extract was washed with 10 ml of HCl (10%) for 3 times, 50 ml of water twice and dried over anhydrous magnesium sulfate. The residual solid was purified by silica gel column chromatography. From the eluate of ethyl acetate/n-hexane (3/1) 56 mg of product (74%) was obtained.

1. extractionThe reaction solution was extracted with 50 ml of ethyl acetate
2. washThe extract was washed with 10 ml of HCl (10%) for 3 times, 50 ml of water twice
3. dry with materialdried over anhydrous magnesium sulfate
4. customThe residual solid was purified by silica gel column chromatography

ORD record

ord-6d87f343c025411bb1f67f975173002c

Source dataset

uspto-grants-1998_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05753692