Sodium Carbonate → 3-(5'-Isopropyl-2'-methoxy-biphenyl-4-yl)-but-2-en-1-ol

Tetrakis(triphenylphoshine)palladium(0) (0.20 g, 0.18 mmol, 4 mol %) was added, under nitrogen, to a stirred solution of (E)-3-(4-bromophenyl)-but-2-en-1-ol (1.0 g, 4.40 mmol) {prepared as detailed in example 50b} in DME (55 ml), and the resulting orange coloured solution stirred at room temperature for 10 min. Aqueous 2M sodium carbonate (13.2 ml, 26.4 mmol) was then added, the mixture stirred for 10 min, then 5-isopropyl-2-methoxyphenylboronic acid (1.28 g, 6.60 mmol) was added, and the reaction mixture heated to 80° C. for 18 h, under reflux. The reaction mixture was diluted with 1N HCl (100 ml) and the products extracted into ethyl acetate (2×100 ml). The combined organic extracts were washed with brine, dried (MgSO4), and evaporated to give the crude product, which was purified by column chromatography on silica gel (1% methanol in dichloromethane eluent) to give the product, 3-(5′-isopropyl-2′-methoxy-biphenyl-4-yl)-but-2-en-1-ol as a colourless oil; 1.15 g (88%).

1. customprepared
2. stirringthe mixture stirred for 10 min
3. temperaturethe reaction mixture heated to 80° C. for 18 h
4. temperatureunder reflux
5. extractionthe products extracted into ethyl acetate (2×100 ml)
6. washThe combined organic extracts were washed with brine
7. dry with materialdried (MgSO4)
8. customevaporated
9. customto give the crude product, which
10. customwas purified by column chromatography on silica gel (1% methanol in dichloromethane eluent)

ORD record

ord-563de7f3c73d4478a8a123c784353a47

Source dataset

uspto-grants-2003_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06555577B1