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Triethylamine → Methyl {3'-[3-(2,4-dichlorophenyl)-2-propynyloxy]-4'-methoxybiphenyl-3-yl}acetate

HRID 2247445
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2247445
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:10]=2)=[CH:5][C:4]=1[O:20][CH2:21][C:22]#[CH:23].[Cl:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=1I.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.[Cu](I)I>[Cl:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=1[C:23]#[C:22][CH2:21][O:20][C:4]1[CH:5]=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:10]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]
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Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 968642,4-Dichloro-1-iodobenzeneHCID 59218932Methyl (4'-methoxy-3'-(2-propynyloxy)biphenyl-3-yl)acetate

Produkt 1

HCID 86594837Methyl {3'-[3-(2,4-dichlorophenyl)-2-propynyloxy]-4'-methoxybiphenyl-3-yl}acetate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysator
HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

9 mg of methyl (4′-methoxy-3′-(2-propynyloxy)biphenyl-3-yl)acetate was dissolved in 0.1 ml of N,N-dimethylformamide, 30 mg of 2,4-dichloroiodobenzene, 2 mg of copper iodide, 2 mg of tetrakistriphenyl phosphine palladium and 0.05 ml of triethylamine were added thereto, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was concentrated to give methyl {3′-[3-(2,4-dichlorophenyl)-2-propynyloxy]-4′-methoxybiphenyl-3-yl}acetate. This product was dissolved in 0.5 ml of ethanol, then 0.1 ml of 5N sodium hydroxide was added thereto, and the mixture was left overnight at room temperature. The reaction mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was concentrated, and the residue was purified by reverse-phase high performance liquid chromatography to give 4.24 mg of the title compound.

Aufarbeitung

  1. washwashed with water
  2. concentrationThe organic layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-650e5569671c45b3a81602ac9ff64696
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07687664B2

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