Hydrochloric Acid → 5-(3-Methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylic acid

HRID 453298Notes

Reaction equation

HRID 453298 reaction equation
[CH3:1][O:2][CH2:3][C:4]#[C:5][C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[C:17]([O:19]CC)=[O:18].[Li+].[OH-].Cl>C1COCC1.CO.O.[Cl-].[Na+].O>[CH3:1][O:2][CH2:3][C:4]#[C:5][C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:7]=1[C:17]([OH:19])=[O:18]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67425118Ethyl 5-(3-methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylate

Product 1

HCID 585518835-(3-Methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylic acidYield 101.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Ethyl 5-(3-methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylate (701 mg, 2.3 mmol) was dissolved in THF/MeOH (1:1, 40 mL) and a solution of LiOH (167 mg, 7.0 mmol) in H2O (10 mL) was added. The reaction was stirred for ˜16 h and the pH adjusted to ˜3 by the addition of 3N HCl. The mixture was poured into brine and extracted with EtOAc. The combined organics were washed with brine, dried (MgSO4) and concentrated to give 5-(3-methoxyprop-1-ynyl)-2-phenylthiazole-4-carboxylic acid (636 mg, 99% yield) as a tan solid.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-976149f5e6b2409db1f4c834029d9cb2
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

Loading…