Sodium Hydroxide → HCID 14452584, compound

HRID 1166215Notes

Reaction equation

HRID 1166215 reaction equation
C([O:3][C:4](=[O:13])[C:5]([C:7]1[S:8][C:9]([CH3:12])=[CH:10][CH:11]=1)=[O:6])C.[OH-].[Na+]>C1COCC1.O>[CH3:12][C:9]1[S:8][C:7]([C:5](=[O:6])[C:4]([OH:13])=[O:3])=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13534763Ethyl (5-methylthiophen-2-yl)(oxo)acetate

Product 1

HCID 14452584HCID 14452584, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (5-methylthiophen-2-yl)-oxo-acetic acid ethyl ester (5.5 g, 28 mmol) in THF (20 ml), water (20 ml), and 50% NaOH (4 ml) was stirred under reflux for 18 hours. The reaction mixture was allowed to cool to ambient temperature. After partial evaporation, the reaction mixture was acidified with 1N HCl and extracted with diethyl ether (2×50 ml). The organic layer was dried over sodium sulfate and concentrated under vacuum to yield (5-methylthiophen-2-yl)-oxo-acetic acid (4.8 g, 100%). 1H NMR (300 MHz, CDCl3) δ8.40 (1H, d, J=4.0 Hz), 6.95 (1H, d, J=3.9 Hz), 2.63 (3H, s).

Workup

  1. temperatureunder reflux for 18 hours
  2. customAfter partial evaporation
  3. extractionextracted with diethyl ether (2×50 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-97c6b5ee788b4d5c844f919bc987c9fd
Source dataset
uspto-grants-2003_09
Patent number
US06613786B2

Reaction notes

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