Propargyl alcohol → 3,3'-(Pyridine-2,6-diyl)di(prop-2-yn-1-ol)

HRID 1828753Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1828753
[CH2:1]([OH:4])[C:2]#[CH:3].Br[C:6]1[CH:11]=[CH:10][CH:9]=[C:8](Br)[N:7]=1>C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:4][CH2:1][C:2]#[C:3][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:3]#[C:2][CH2:1][OH:4])[N:7]=1

Komponenten

5

Edukt 2

HCID 7859Propargyl alcoholHCID 122742,6-Dibromopyridine

Produkt 1

HCID 220583863,3'-(Pyridine-2,6-diyl)di(prop-2-yn-1-ol)Ausbeute 134,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

Pd(Ph3P)4 (99 mg, 2%), CuBrSMe2 (38 mg) and propargyl alcohol (1.3 ml, 21 mmol) are added successively to a solution of 2,6-dibromopyridine (5.0 g, 21.1 mmol) in triethylamine (120 ml), and the mixture is stirred at RT for 10 min and then under reflux at 80° C. for 2 h. After cooling, the reaction mixture is filtered off through kieselguhr, and the filter cake is washed with ethyl acetate (20 ml). The organic phase is concentrated under reduced pressure. Further purification is carried out by chromatography [toluene/acetone (7:3)] on a silica gel column. This gives the title compound (2.65 g) as a colorless solid. TLC, silica gel (glass plates) [toluene/acetone (7:3)], Rf=0.15.

Aufarbeitung

  1. temperatureunder reflux at 80° C. for 2 h
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture is filtered off through kieselguhr
  4. washthe filter cake is washed with ethyl acetate (20 ml)
  5. concentrationThe organic phase is concentrated under reduced pressure
  6. customFurther purification

Quellen und Nachweise

ORD-Eintrag
ord-fbc4ad8d0d0a466e84e6063d5e58290b
Quelldatensatz
uspto-grants-2006_06
Patentnummer
US07060716B2

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