Hydrochloric Acid → 4'-Methyl-5-(thiazol-2-yloxy)biphenyl-3-carboxylic acid

HRID 1845268Notes

Reaction equation

HRID 1845268 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[S:16][CH:17]=[CH:18][N:19]=3)[CH:11]=[C:10]([C:20]([O:22]C)=[O:21])[CH:9]=2)=[CH:4][CH:3]=1.[OH-].[Li+].Cl>O1CCCC1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]([O:14][C:15]3[S:16][CH:17]=[CH:18][N:19]=3)[CH:11]=[C:10]([C:20]([OH:22])=[O:21])[CH:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58187983Methyl 4'-methyl-5-(thiazol-2-yloxy)biphenyl-3-carboxylate

Product 1

HCID 581880714'-Methyl-5-(thiazol-2-yloxy)biphenyl-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 4′-methyl-5-(thiazol-2-yloxy)biphenyl-3-carboxylate (560 mg, 1.6 mmol) in tetrahydrofuran (20 mL) was added 2.5 M aqueous lithium hydroxide solution (6.7 mL, 17 mmol). After being stirred at room temperature overnight, the mixture was acidified to pH=5 by addition of 2N aq. HCl and extracted with EtOAc. The organic layer was dried over sodium sulfate, and concentrated to afford the title product. 1H NMR (CD3OD, 400 MHz): 8.18 (t, 1H, J=1.6 Hz), 7.82 (dd, 1H, J=2.4, 1.2 Hz), 7.74 (t, 1H, J=2.0 Hz), 7.57 (d, 2H, J=8.0 Hz), 7.30 (d, 2H, J=8.4 Hz), 7.28 (d, 1H, J=4.0 Hz), 7.13 (d, 1H, J=4.0 Hz), 2.39 (s, 3H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c4006a240a99444384350e2d532e1492
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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