Sodium Hydroxide → 5-(3-Hydroxy-1-propynyl)-2,2'-bithiophene

Hydroxy-1-propyne (48 mg) was dissolved in benzene (1 ml). 5-Iodo-2,2'-bithiophene (0.1 g) was added immediately and stirred. A mixture of CuI (0.05 g), benzyltriethylammonium chloride (0.05 g), catalyst Pd(PPh3)4 (0.1 g) and 3 ml of NaOH solution (2.5N) were mixed together at room temperature and stirred for 2 hours. NH4Cl solution (4 ml) was then added. The reaction solution was extracted with 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, eluted with ethyl acetate/n-hexane (3/1) to yield 56 mg of the product (74%).

1. additionwere mixed together at room temperature
2. stirringstirred for 2 hours
3. extractionThe reaction solution was extracted with ethyl acetate
4. washThe extract was washed with 10 ml of HCl (10%) for 3 times, 50 ml of water twice
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe residual solid was purified by silica gel column chromatography
7. washeluted with ethyl acetate/n-hexane (3/1)

ORD-Eintrag

ord-9cdc6e4007b14e97bafd48cf42c7f12d

Quelldatensatz

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05741811