Phenol → 4'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester
Reaktionsgleichung
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[C:35](C2C=CC(CSCCO)=CC=2)=[CH:36][CH:37]=[CH:38][CH:39]=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>>[CH2:29]([O:31][C:32]([C:34]1[C:39]([C:12]2[CH:13]=[CH:14][C:15]([CH2:18][S:19][CH2:20][CH2:21][O:22][C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[CH:16][CH:17]=2)=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:33])[CH3:30]Komponenten
Edukt 4
Produkt 1
Versuchsvorschrift
4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester was prepared as described for 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester. 4′-(2-hydroxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester (1.65 g, 5.21 mmol, 1 eq.) was treated with phenol (0.69 g, 7.29 mmol, 1.4 eq.), triphenylphosphine (1.91 g, 7.29 mmol, 1.4 eq.), and diisopropyl azidocarboxylate (1.47 g, 1.44 mL, 7.29 mmol, 1.4 eq.). When complete, the reaction was worked up and the product purified by silica gel flash chromatography using 7.5% EtOAc in hexane as the mobile phase. Fractions containing the product were pooled and the solvent removed in vacuo leaving 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester (1.40 g, 68% yield) as a yellow oil.
Aufarbeitung
- custom4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester was prepared
- customthe product purified by silica gel flash chromatography
- additionFractions containing the product
- customthe solvent removed in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-205cf55e793b4974a0126ffef6531b88
- Quelldatensatz
- uspto-grants-2006_11
- Patentnummer
- US07132456B2
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