Triphenylphosphine → 2-(2,6-Diethyl-phenyl)-5-[1-(3-ethoxy-phenoxy)-butyl]4-ethoxy-pyridine

HRID 1392646

Reaktionsgleichung

Reaktionsgleichung von HRID 1392646
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[N:16]=[CH:15][C:14]([CH:17]([OH:21])[CH2:18][CH2:19][CH3:20])=[C:13]([O:22][CH2:23][CH3:24])[CH:12]=1)[CH3:2].[CH2:25]([O:27][C:28]1[CH:29]=[C:30](O)[CH:31]=[CH:32][CH:33]=1)[CH3:26].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[NH4+].[Cl-]>C1COCC1.CCCCCC>[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]([O:22][CH2:23][CH3:24])[C:14]([CH:17]([O:21][C:32]2[CH:31]=[CH:30][CH:29]=[C:28]([O:27][CH2:25][CH3:26])[CH:33]=2)[CH2:18][CH2:19][CH3:20])=[CH:15][N:16]=1)[CH3:2]

Komponenten

8

Edukt 5

HCID 11776TriphenylphosphineHCID 25517Ammonium ChlorideHCID 693063-EthoxyphenolHCID 5462977Diethyl azodicarboxylateHCID 596783161-[6-(2,6-Diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-butan-1-ol

Produkt 1

HCID 596782592-(2,6-Diethyl-phenyl)-5-[1-(3-ethoxy-phenoxy)-butyl]4-ethoxy-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

A mixture of 1-[6-(2,6-diethyl-phenyl)-4-ethoxy-pyridin-3-yl]-butan-1-ol (67 mg, 0.20 mmol), 3-ethoxy-phenol (34 mg, 0.25 mmol), triphenylphosphine (65 mg, 0.25 mmol), and DEAD (36 mg, 0.25 mmol) in THF (1 mL) is stirred at room temperature overnight. Aqueous NH4Cl solution (5 mL) and hexane (10 mL) are added to the mixture, and the organic layer is separated. The organic layer is washed with NaHCO3 solution, brine, dried over Na2SO4, and concentrated. The residue is purified by PTLC to give 2-(2,6-diethyl-phenyl)-5-[1-(3-ethoxy-phenoxy)-butyl]4-ethoxy-pyridine. 1H NMR (CDCl3) 8.55 (s, 1H), 7.27 (m, 1H), 7.07-7.14 (m, 3H), 6.73 (s, 1H), 6.43-6.49 (m, 3H), 5.57 (m, 1H), 4.13 (q, 2H), 3.95 (q, 2H), 2.56-2.37 (m, 4H), 1.85-2.05 (m, 2H), 1.40-1.60 (m, 5H), 1.37 (t, 3H), 0.96-1.08 (m, 9H).

Aufarbeitung

  1. customthe organic layer is separated
  2. washThe organic layer is washed with NaHCO3 solution, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue is purified by PTLC

Quellen und Nachweise

ORD-Eintrag
ord-7524c919d5414fcc93309a0cfa05c5eb
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07342115B2

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