Hydrochloric Acid → 5-(2-(1,3-Dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylic acid

HRID 1799118Notes

Reaction equation

HRID 1799118 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][CH2:7][C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[C:19]([O:21]CC)=[O:20].[Li+].[OH-].Cl>CO.C1COCC1.O.[Cl-].[Na+].O>[O:3]1[CH2:4][CH2:5][O:1][CH:2]1[CH2:6][CH2:7][C:8]1[S:12][C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][C:9]=1[C:19]([OH:21])=[O:20]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67434696Ethyl 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylate

Product 1

HCID 585519085-(2-(1,3-Dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylic acidYield 75%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Ethyl 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylate (2.6 g, 7.9 mmol) was dissolved in MeOH/THF (1:1, 60 mL) and a solution of LiOH (378 mg, 15.7 mmol) in H2O (15 mL) was added. The reaction was stirred for ˜5 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. The crude product was crystallized from EtOAc to give 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylic acid (1.8 g, 75% yield).

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude product was crystallized from EtOAc

Sources & evidence

ORD record
ord-1e746c0d83bc4567ac42d22fe8ca3095
Source dataset
uspto-grants-2013_01
Patent number
US08343997B2

Reaction notes

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