Sodium Hydroxide → 4-Methyl-5-naphthalen-1-yl-thiazole-2-carboxylic acid

HRID 12453

Reaction equation

HRID 12453 reaction equation
C([O:3][C:4]([C:6]1[S:7][C:8]([C:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14][CH:13]=2)=[C:9]([CH3:11])[N:10]=1)=[O:5])C.[OH-].[Na+]>O.C1COCC1>[CH3:11][C:9]1[N:10]=[C:6]([C:4]([OH:5])=[O:3])[S:7][C:8]=1[C:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 593384494-Methyl-5-naphthalen-1-yl-thiazole-2-carboxylic acid ethyl ester

Product 1

HCID 593378204-Methyl-5-naphthalen-1-yl-thiazole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methyl-5-naphthalen-1-yl-thiazole-2-carboxylic acid ethyl ester (30 mg, 0.10 mmol) in water (1 ml) and THF (1 ml) is added sodium hydroxide (0.2 mL, 1M, 0.20 mmol). The reaction mixture is stirred at rt for 1 hr, and then extracted with ethyl ether (30 mL). The aqueous layer is acidified to pH<7.0 by phosphate buffer and then extracted with EtOAc (2×50 mL). The combined organic layers are washed with brine, dried over MgSO4, and then concentrated. The crude product is used in the next step without further purification.

Workup

  1. extractionextracted with ethyl ether (30 mL)
  2. extractionextracted with EtOAc (2×50 mL)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product is used in the next step without further purification

Sources & evidence

ORD record
ord-a99f6adcd06645219a6b3df332299ba2
Source dataset
uspto-grants-2010_06
Patent number
US07728009B1

Linked notes

Loading…