Lithium Hydroxide → 4'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid

HRID 719693Notes

Reaction equation

HRID 719693 reaction equation
O(CCSCC1C=CC(C2C=CC=C(C(O)=O)C=2)=CC=1)C1C=CC=CC=1.C([O:29][C:30]([C:32]1[C:33]([C:38]2[CH:43]=[CH:42][C:41]([CH2:44][S:45][CH2:46][CH2:47][O:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)=[CH:40][CH:39]=2)=[CH:34][CH:35]=[CH:36][CH:37]=1)=[O:31])C.[OH-].[Li+]>C1COCC1>[O:48]([CH2:47][CH2:46][S:45][CH2:44][C:41]1[CH:42]=[CH:43][C:38]([C:33]2[C:32]([C:30]([OH:31])=[O:29])=[CH:37][CH:36]=[CH:35][CH:34]=2)=[CH:39][CH:40]=1)[C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1

Participants

5

Reactant 3

HCID 3939Lithium HydroxideHCID 218999924'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acidHCID 586105774'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester

Product 1

HCID 218999824'-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid was prepared as described for 4′-(2-phenoxy-ethylsulfanylmethyl)-biphenyl-3-carboxylic acid. 4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid ethyl ester (1.6 g, 4.08 mmol, 1 eq.) in 30% aqueous THF was treated with lithium hydroxide (0.29 g, 12.24 mmol, 3 eq.). When complete, the reaction was worked up as described and the resulting oil purified via silica gel flash chromatography using 50% 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 (1.44 g, 97% yield) as an orange oil.

Workup

  1. custom4′-(2-Phenoxy-ethylsulfanylmethyl)-biphenyl-2-carboxylic acid was prepared
  2. customthe resulting oil purified via silica gel flash chromatography
  3. additionFractions containing the product
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-a47d455a4bf348278aebb9ac850ced1b
Source dataset
uspto-grants-2006_11
Patent number
US07132456B2

Reaction notes

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