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

Temperatur

135 °C

A mixture of 3-bromopyridine (11.22 g, 70.58 mmol), (2S)-4-penten-2-ol (5.00 g, 58.05 mmol), palladium(II) acetate (527 mg, 2.35 mmol), tri-o-tolylphosphine (1.79 g, 5.88 mmol), triethylamine (30 mL, 216 mmol) and acetonitrile (30 mL) was 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 (20 mL) was added and the mixture was extracted with chloroform (4×50 mL). The combined chloroform extracts were dried (K2CO3), filtered, and concentrated by rotary evaporation, producing a pale-yellow oil (6.00 g). 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, affording 3.95 g (41.7%) 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 (20 mL) was added
4. extractionthe mixture was extracted with chloroform (4×50 mL)
5. dry with materialThe combined chloroform extracts were dried (K2CO3)
6. filtrationfiltered
7. concentrationconcentrated by rotary evaporation

ORD-Eintrag

ord-107a984f4166462bad66172f1e959e6c

Quelldatensatz

uspto-grants-2005_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06958399B2