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

HRID 719732Notes

Reaction equation

HRID 719732 reaction equation
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=CC=2CSCCO)=[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:14]2[CH:13]=[CH:12][CH:17]=[CH:16][C:15]=2[CH2:18][S:19][CH2:20][CH2:21][O:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[CH:36][CH:35]=1)=[O:33])[CH3:30]

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 586105812'-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid ethyl esterHCID 586105864'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester

Product 1

HCID 586105922'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-4-carboxylic acid ethyl ester was synthesized as described for 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester. 2′-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl4-carboxylic acid ethyl ester (4.15 g, 13.12 mmol, 1 eq.) in anhydrous THF was treated with phenol (1.61 g, 17.06 mmol, 1.3 eq.), triphenylphosphine (4.47 g, 17.06 mmol, 1.3 eq.), and diisopropyl azidocarboxylate (3.45 g, 17.06 mmol, 1.3 eq.). When complete, the reaction was worked up as described leaving a yellow oil.

Workup

  1. customas described leaving a yellow oil

Sources & evidence

ORD record
ord-2730b8dfd76140f588b0ba4b95faff00
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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