Triethylamine → (2S)-(4E)-5-(5-Isopropoxy-3-pyridyl)-4-penten-2-ol

Temperature

135 °C

A mixture of 5-isopropoxy-3-bromopyridine (12.56 g, 58.13 mmol), (2S)-4-penten-2-ol (5.00 g, 58.05 mmol), palladium(II) acetate (130 mg, 0.58 mmol), tri-o-tolylphosphine (706 mg, 2.32 mmol), triethylamine (35 mL, 252 mmol) and acetonitrile (35 mL) were heated in a sealed glass tube at 130-140° C. for 8 h. The reaction mixture was cooled to ambient temperature. The solvent was removed under reduced pressure on a rotary evaporator. Water (50 mL) was added and the mixture was extracted with chloroform (3×50 mL). The combined chloroform extracts were dried (K2CO3), filtered, and concentrated by rotary evaporation. The crude product was purified by column chromatography over silica gel, eluting with chloroform-acetone (95:5, v/v). Selected fractions were combined and concentrated by rotary evaporation, producing 7.80 g (60.7%) of a pale-yellow oil.

1. temperatureThe reaction mixture was cooled to ambient temperature
2. customThe solvent was removed under reduced pressure on a rotary evaporator
3. additionWater (50 mL) was added
4. extractionthe mixture was extracted with chloroform (3×50 mL)
5. dry with materialThe combined chloroform extracts were dried (K2CO3)
6. filtrationfiltered
7. concentrationconcentrated by rotary evaporation
8. customThe crude product was purified by column chromatography over silica gel
9. washeluting with chloroform-acetone (95:5
10. concentrationconcentrated by rotary evaporation

ORD record

ord-a4ad68145378498cb4007b4c3de14308

Source dataset

uspto-grants-2005_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06979695B2