Diethylamine → HCID 11779758, Verbindung

HRID 1494117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1494117
[OH:1][CH:2]([CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][O:12]1)[CH2:3][C:4]#[CH:5].C(NCC)C.Br[C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1>[Cu]I>[N:25]1[CH:26]=[CH:27][CH:28]=[C:23]([C:5]#[C:4][CH2:3][CH:2]([OH:1])[CH2:6][CH2:7][CH2:8][CH2:9][O:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][O:12]2)[CH:24]=1

Komponenten

5

Edukt 3

HCID 8021DiethylamineHCID 122863-BromopyridineHCID 10353657HCID 10353657, Verbindung

Produkt 1

HCID 11779758HCID 11779758, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Katalysator

Versuchsvorschrift

A mixture of 5.84 g (25.8 mmol) 4-hydroxy-8-(2-tetrahydropyranyloxy)-1-octyne, 4.7 mL diethylamine, 10 mL (100 mmol) 3-bromopyridine, 0.032 g copper (I) iodide, and 0.187 g bis-triphenylphosphine palladium (II) chloride is stirred at room temperature for 18 hours. The solvent is evaporated and the residue taken up in ether. The ether layer is washed with saturated aqueous sodium bicarbonate, water, brine, dried, filtered and evaporated to get an amber oil which is purified by chromatography using ether as the eluent to give 1-(3-pyridyl)-4-hydroxy-8-(2-tetrahydropyranyloxy)-1-octyne; NMR (CDCl3): delta 4.6 (brs,1H), 2.6 (d,2H).

Aufarbeitung

  1. customThe solvent is evaporated
  2. washThe ether layer is washed with saturated aqueous sodium bicarbonate, water, brine
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customto get an amber oil which
  7. customis purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c62d6b306306449789e8a7d4212c8fd7
Quelldatensatz
uspto-grants-1991_06
Patentnummer
US05025025

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