HCID 69968949, compound → HCID 22997650, compound

HRID 1166202Notes

Reaction equation

HRID 1166202 reaction equation
C([O:3][C:4](=[O:13])[C:5]([C:7]1[S:8][C:9]([I:12])=[CH:10][CH:11]=1)=[O:6])C>O1CCOCC1.[OH-].[K+]>[I:12][C:9]1[S:8][C:7]([C:5](=[O:6])[C:4]([OH:13])=[O:3])=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 69968949HCID 69968949, compound

Product 1

HCID 22997650HCID 22997650, compound

Reagents, catalysts & solvents 2

HCID 14797Potassium HydroxideSolventHCID 312751,4-DioxaneSolvent

Procedure

(5-Iodothiophen-2-yl)-oxo-acetic acid ethyl ester (0.298 g, 0.96 mmol) was dissolved in 1,4 dioxane (4 ml) and 20% KOH (0.5 ml). The reaction mixture was stirred at ambient temperature for 4 hours then volatile solvent was removed by rotary evaporation. The residue was dissolved in 5 ml water and extracted with diethyl ether (35 ml). The aqueous layer was acidified to pH 3-4 with glacial acetic acid, and extracted with ethyl acetate (3×35 ml). The combined ethyl acetate extracts were dried over Na2SO4 and concentrated under vacuum to provide Preparation 1c (92 mg, 34%). MS (M−H)−: 280.77; 1H NMR (300 MHz, DMSO-d6) δ7.59 (1H, d, J=3.9 Hz), 7.50 (1H, d, J=4.0 Hz).

Workup

  1. customvolatile solvent was removed by rotary evaporation
  2. dissolutionThe residue was dissolved in 5 ml water
  3. extractionextracted with diethyl ether (35 ml)
  4. extractionextracted with ethyl acetate (3×35 ml)
  5. dry with materialThe combined ethyl acetate extracts were dried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customto provide

Sources & evidence

ORD record
ord-d1e5ffd428f64fcd96be757fc733254b
Source dataset
uspto-grants-2003_09
Patent number
US06613786B2

Reaction notes

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