Phenol → 4'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid ethyl ester

HRID 719684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 719684
C(OC(C1C=C([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][S:19][CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:14][CH:13]=2)C=CC=1)=O)C.[CH2:29]([O:31][C:32]([C:34]1[CH:39]=[CH:38][C:37](C2C=CC(CSCCO)=CC=2)=[CH:36][CH:35]=1)=[O:33])[CH3:30].C1(O)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH2:29]([O:31][C:32]([C:34]1[CH:39]=[CH:38][C:37]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][S:19][CH2:20][CH2:21][O:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[CH:14][CH:13]=2)=[CH:36][CH:35]=1)=[O:33])[CH3:30]

Komponenten

6

Edukt 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 586105864'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl esterHCID 586106004'-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid ethyl ester

Produkt 1

HCID 586105784'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid ethyl esterAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid ethyl ester was prepared as described for 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester. 4′-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid ethyl ester (3.11 g, 9.83 mmol, 1 eq.) in anhydrous THF (100 mL) was treated with phenol (1.29 g, 13.76 mmol, 1.4 eq.), triphenylphosphine (3.61 g, 13.76 mmol, 1.4 eq.), and diisopropyl azidocarboxylate (2.78 g, 2.71 mL, 13.76 mmol, 1.4 eq.) as described. When the reaction was complete, the reaction was worked up and the product purified via silica gel flash chromatography leaving 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl4-carboxylic acid ethyl ester (3.82 g, 99% yield) as a yellow oil.

Aufarbeitung

  1. custom4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid ethyl ester was prepared
  2. customthe product purified via silica gel flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-5f0765b950eb44bea68aae3daaf4992d
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07132456B2

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