Ethyl Acetate → 2-(4-chlorophenyl)-N-(3'-methoxy-4'-pent-2-ynyloxy-biphenyl-2-yl)-2-prop-2-ynyloxy-acetamide

HRID 1375224

Reaktionsgleichung

Reaktionsgleichung von HRID 1375224
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([O:27][CH2:28][C:29]#[CH:30])[C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([O:25][CH3:26])[CH:19]=2)=[O:10])=[CH:4][CH:3]=1.C[O-].[Na+].[CH2:34](Cl)[C:35]#[C:36][CH2:37][CH3:38].C(OCC)(=O)C>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([O:27][CH2:28][C:29]#[CH:30])[C:9]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]2[CH:23]=[CH:22][C:21]([O:24][CH2:34][C:35]#[C:36][CH2:37][CH3:38])=[C:20]([O:25][CH3:26])[CH:19]=2)=[O:10])=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 897641-Chloro-2-pentyneHCID 10942334Sodium MethoxideHCID 210798502-(4-Chlorophenyl)-N-(4'-hydroxy-3'-methoxy-biphenyl-2-yl)-2-prop-2-ynyloxy-acetamide

Produkt 1

HCID 115187642-(4-chlorophenyl)-N-(3'-methoxy-4'-pent-2-ynyloxy-biphenyl-2-yl)-2-prop-2-ynyloxy-acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of 1.3 g (3.1 mmol) 2-(4-chloro-phenyl)-N-(4′-hydroxy-3′-methoxy-biphenyl-2-yl)-2-prop-2-ynyloxy-acetamide, 6.0 ml (6.0 mmol) of a 1 M solution of sodium methoxide in methanol and 0.5 g (4.7 mmol) 2-pentynyl chloride in 50 ml of methanol is heated to reflux for 3 hours. After cooling, the reaction mixture is poured into ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate and evaporated. The remaining product is subjected to flash-chromatography (ethyl acetate/hexane 4:6) to yield 2-(4-chlorophenyl)-N-(3′-methoxy-4′-pent-2-ynyloxy-biphenyl-2-yl)-2-prop-2-ynyloxy-acetamide as yellow oil.

Aufarbeitung

  1. temperatureto reflux for 3 hours
  2. temperatureAfter cooling
  3. washThe organic layer is washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7427b86e1ded4cda9ac7c186b963323a
Quelldatensatz
uspto-grants-2007_01
Patentnummer
US07166746B2

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