Propargyl alcohol → 3-(5-Bromopyridin-2-yl)prop-2-yn-1-ol

HRID 2108034

Reaktionsgleichung

Reaktionsgleichung von HRID 2108034
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[CH2:9]([OH:12])[C:10]#[CH:11]>C(NCC)C.[Cu]I>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:11]#[C:10][CH2:9][OH:12])=[N:3][CH:4]=1

Komponenten

5

Edukt 2

HCID 7859Propargyl alcoholHCID 693532,5-Dibromopyridine

Produkt 1

HCID 139797303-(5-Bromopyridin-2-yl)prop-2-yn-1-olAusbeute 80,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 8021DiethylamineLösungsmittel

Versuchsvorschrift

Copper (I) iodide (10 mg) was added to a solution of 2,5-dibromopyridine (4.74 g), propargyl alcohol (1.34 g) and BTPC (75 mg) in diethylamine (50 ml) and the mixture stirred overnight (18 h), under nitrogen. The solution was evaporated in vacuo and the residue treated with 8% sodium bicarbonate (50 ml) and partitioned with dichloromethane (3×50 ml). The combined extracts were dried and evaporated and the residual semi-solid purified by FCC. Eluting with ether afforded the title compound (3.43 g) as fawn crystals m.p. 121°-122°.

Aufarbeitung

  1. customThe solution was evaporated in vacuo
  2. additionthe residue treated with 8% sodium bicarbonate (50 ml)
  3. custompartitioned with dichloromethane (3×50 ml)
  4. customThe combined extracts were dried
  5. customevaporated
  6. customthe residual semi-solid purified by FCC
  7. washEluting with ether

Quellen und Nachweise

ORD-Eintrag
ord-3b0770f191704598b3c43a06f4196909
Quelldatensatz
uspto-grants-1990_06
Patentnummer
US04937251

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