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

HRID 719718Notes

Reaction equation

HRID 719718 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[C:35](C2C=CC=CC=2CSCCO)=[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>C1COCC1>[CH2:29]([O:31][C:32]([C:34]1[C:39]([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:38][CH:37]=[CH:36][CH:35]=1)=[O:33])[CH3:30]

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 586105864'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl esterHCID 586105992'-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester

Product 1

HCID 586106022'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester was synthesized as described for 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid ethyl ester. 2′-(2-Hydroxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester (5.0 g, 15.80 mmol, 1 eq.) in anhydrous THF was treated with phenol (2.08 g, 22.12 mmol, 1.4 eq.), triphenylphosphine (5.80 g, 22.12 mmol, 1.4 eq.), and diisopropyl azidocarboxylate (4.47 g, 22.12 mmol, 1.4 eq.). When complete, the reaction was worked up as described leaving an orange oil.

Workup

  1. customas described leaving an orange oil

Sources & evidence

ORD record
ord-fd09d150f207420390ee574754def0bf
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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