Acetonitrile → (2R)-(4E)-5-(3-pyridyl)4-penten-2-ol

HRID 489747

Reaktionsgleichung

Reaktionsgleichung von HRID 489747
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:8][C@@H:9]([OH:13])[CH2:10][CH:11]=[CH2:12].C(N(CC)CC)C.C(#N)C>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[N:4]1[CH:5]=[CH:6][CH:7]=[C:2](/[CH:12]=[CH:11]/[CH2:10][C@H:9]([OH:13])[CH3:8])[CH:3]=1

Komponenten

8

Edukt 4

HCID 6342AcetonitrileHCID 8471TriethylamineHCID 122863-BromopyridineHCID 6999724(2R)-pent-4-en-2-ol

Produkt 1

HCID 66745560(2R)-(4E)-5-(3-pyridyl)4-penten-2-olAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 80271Tri-o-tolylphosphineKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 3-bromopyridine (9.17 g, 58.04 mmol), (2R)-4-penten-2-ol (6.00 g, 69.65 mmol), palladium(II) acetate (130 mg, 0.58 mmol), tri-o-tolylphosphine (710 mg, 2.32 mmol), triethylamine (34.7 mL, 249.5 mmol), and acetonitrile (35 mL) were heated in a sealed glass tube at 140° C. for 14 h. The reaction mixture was cooled to ambient temperature, diluted with water, and extracted with chloroform (3×200 mL). The combined chloroform extracts were dried over sodium sulfate, filtered, and concentrated by rotary evaporation to give 6.17 g (65.2%) of a pale-yellow oil.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionextracted with chloroform (3×200 mL)
  3. dry with materialThe combined chloroform extracts were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-3734bd6563844b058ed6bd49d61cfd10
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06979695B2

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