Triphenylphosphine → 5-[2-(2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-yloxy)-1,1-dimethyl-ethyl]-thiophene-2-carboxylic acid methyl ester

HRID 660986Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 660986
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10]([CH3:14])([CH3:13])[CH2:11][OH:12])=[CH:8][CH:9]=1)=[O:4].[CH3:15][C:16]1[CH:21]=[C:20](O)[CH:19]=[C:18]([CH3:23])[C:17]=1[C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1(C)C=CC=CC=1.CO>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:10]([CH3:14])([CH3:13])[CH2:11][O:12][C:20]2[CH:21]=[C:16]([CH3:15])[C:17]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:31])([F:33])[F:32])=[CH:26][CH:25]=3)=[C:18]([CH3:23])[CH:19]=2)=[CH:8][CH:9]=1)=[O:4]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 569717492,6-Dimethyl-4'-(trifluoromethyl)-[1,1'-biphenyl]-4-olHCID 67484466Methyl 5-(1-hydroxy-2-methylpropan-2-yl)thiophene-2-carboxylate

Produkt 1

HCID 593559295-[2-(2,6-Dimethyl-4'-trifluoromethyl-biphenyl-4-yloxy)-1,1-dimethyl-ethyl]-thiophene-2-carboxylic acid methyl esterAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 5-(2-hydroxy-1,1-dimethyl-ethyl)-thiophene-2-carboxylic acid methyl ester (0.436 g, 2.04 mmol), 2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-ol (0.596 g, 2.24 mmol), and PPh3 (0.793 g, 3.02 mmol) is dissolved in toluene (20 mL), treated with 1,1′-(azodicarbonyl)dipiperidine (ADDP, 0.763 g, 3.02 mmol), and stirred overnight at 80° C. The mixture is then cooled to rt, diluted with MeOH until homogeneous, and concentrated. The residue is loaded onto silica gel and eluted using hexanes with an ethyl acetate gradient from 0% to 40% to afford 5-[2-(2,6-dimethyl-4′-trifluoromethyl-biphenyl-4-yloxy)-1,1-dimethyl-ethyl]-thiophene-2-carboxylic acid methyl ester (0.394 g, 42%). MS (ES): 463.3 [M+H]+.

Aufarbeitung

  1. temperatureThe mixture is then cooled to rt
  2. concentrationconcentrated
  3. washeluted

Quellen und Nachweise

ORD-Eintrag
ord-996cda2a683641c991574375c43bd1dd
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084489B2

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