Triphenylphosphine → (+/-)-5-[1-(4'-Tert-butyl-2,6-dimethyl-biphenyl-4-yloxy)-ethyl]-thiophene-2-carboxylic acid ethyl ester

HRID 661000

Reaktionsgleichung

Reaktionsgleichung von HRID 661000
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([CH:11]([OH:13])[CH3:12])=[CH:9][CH:10]=1)=[O:5])[CH3:2].[C:14]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:29]([CH3:30])=[CH:28][C:27](O)=[CH:26][C:25]=2[CH3:32])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].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>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([CH:11]([O:13][C:27]2[CH:28]=[C:29]([CH3:30])[C:24]([C:21]3[CH:22]=[CH:23][C:18]([C:14]([CH3:16])([CH3:15])[CH3:17])=[CH:19][CH:20]=3)=[C:25]([CH3:32])[CH:26]=2)[CH3:12])=[CH:9][CH:10]=1)=[O:5])[CH3:2]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 533020184'-Tert-butyl-2,6-dimethylbiphenyl-4-OLHCID 59355961Ethyl 5-(1-hydroxyethyl)thiophene-2-carboxylate

Produkt 1

HCID 67484337(+/-)-5-[1-(4'-Tert-butyl-2,6-dimethyl-biphenyl-4-yloxy)-ethyl]-thiophene-2-carboxylic acid ethyl esterAusbeute 671 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of (±)-5-(1-hydroxy-ethyl)-thiophene-2-carboxylic acid ethyl ester (0.416 g, 2.08 mmol), 4′-tert-butyl-2,6-dimethyl-biphenyl-4-ol (0.561 g, 2.20 mmol), and PPh3 (0.787 g, 3.00 mmol) is dissolved in toluene (19 mL) and treated with 1,1′-(azodicarbonyl)dipiperidine (ADDP, 0.760 g, 3.01 mmol) and stirred overnight at rt. The mixture is diluted with MeOH until homogeneous and conc. The residue is loaded onto silica gel and eluted using hexanes with an ethyl acetate gradient from 0% to 40% giving (±)-5-[1-(4′-tert-butyl-2,6-dimethyl-biphenyl-4-yloxy)-ethyl]-thiophene-2-carboxylic acid ethyl ester (0.604 g, 671%) as a clear syrup.

Aufarbeitung

  1. washeluted

Quellen und Nachweise

ORD-Eintrag
ord-1cf785b3ae694482950d6fcc298a9d3d
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084489B2

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