Pentachlorophenol → HCID 53248609, Verbindung

HRID 77347

Reaktionsgleichung

Reaktionsgleichung von HRID 77347
[CH2:1]([O:3][P:4]([O:19][CH2:20][CH3:21])([O:6][C:7]1[CH:12]=[CH:11][C:10](/[C:13](/[CH3:18])=[CH:14]/[C:15]([OH:17])=[O:16])=[CH:9][CH:8]=1)=[O:5])[CH3:2].[Cl:22][C:23]1[C:28](O)=[C:27]([Cl:30])[C:26]([Cl:31])=[C:25]([Cl:32])[C:24]=1[Cl:33].C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH2:1]([O:3][P:4]([O:19][CH2:20][CH3:21])([O:6][C:7]1[CH:8]=[CH:9][C:10](/[C:13](/[CH3:18])=[CH:14]/[C:15]([O:17][C:28]2[C:27]([Cl:30])=[C:26]([Cl:31])[C:25]([Cl:32])=[C:24]([Cl:33])[C:23]=2[Cl:22])=[O:16])=[CH:11][CH:12]=1)=[O:5])[CH3:2]

Komponenten

6

Edukt 3

HCID 992PentachlorophenolHCID 10868DicyclohexylcarbodiimideHCID 53248608HCID 53248608, Verbindung

Produkt 1

HCID 53248609HCID 53248609, VerbindungAusbeute 72,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 10b (2.0 g, 6.4 mmol), pentachlorophenol (1.9 g, 7.0 mmol), DCC (1.6 g, 7.7 mmol) and DMAP (0.08 g, 0.64 mmol) in 100 mL of EtOAc was stirred at room temperature for 24 h. The mixture was filtered through celite and the solvent removed in vacuo. The crude product was purified by silica gel chromatography eluting with 25% EtOac-hexanes to give 2.6 g (72%) of 11b1 as white solid. 1H NMR (CDCl3, 300 MHz) δ 1.26-1.32 (m, 6H), 2.54 (d, J=1.2 Hz, 3H), 4.12-4.21 (m, 4H), 6.34 (d, J=1.2 Hz, 1H), 7.2 (d, J=8.7 Hz, 2H), 7.49 (d, J=8.7 Hz, 2H). 11C NMR (CDCl3, 75.0 MHz) δ 16.0, 16.1, 18.4, 64.8, 64.8, 68.9, 113.4, 120.2, 120.3, 128.0, 128.1, 131.2, 131.9, 137.8, 141.9, 144.3, 152.1, 160.6, 161.9. HRMS (M+H) calc, 560.9362; found, 560.9197.

Aufarbeitung

  1. filtrationThe mixture was filtered through celite
  2. customthe solvent removed in vacuo
  3. customThe crude product was purified by silica gel chromatography
  4. washeluting with 25% EtOac-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-45336e3cdda04410bbba6192b600804b
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08841257B2

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