Water → 3-Acetyl-5-chloro-2-phenoxythiophene

HRID 1004173Notes

Reaction equation

HRID 1004173 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[C:10]([C:13]1[CH:17]=[C:16]([Cl:18])[S:15][C:14]=1Cl)(=[O:12])[CH3:11].O>CN(C=O)C.[Cu]I>[C:10]([C:13]1[CH:17]=[C:16]([Cl:18])[S:15][C:14]=1[O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)(=[O:12])[CH3:11]

Participants

7

Reactant 4

HCID 962WaterHCID 996PhenolHCID 24758Sodium hydrideHCID 1189201-(2,5-Dichloro-3-thienyl)ethan-1-one

Product 1

HCID 232276103-Acetyl-5-chloro-2-phenoxythiopheneYield 67%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of phenol (1.22 g, 13 mM) and NaH (60% oil dispersion, 0.52 g, 13 mM) in DMF (25 mL) was stirred for 40 minutes at room temperature. 3-Acetyl-2,5-dichlorothiophene (1.95 g, 10 mM) and copper (I) iodide (50 mg) was added to the above mixture, and the resulting mixture was heated at 130° C. for 1.5 hours. After cooling, the mixture was poured into water. The whole was extracted with ethyl acetate-hexane (1:1, 200 mL×1, 100 mL×1), and the combined organic layers washed with water, brine, dried over MgSO4, and concentrated in vacuo. Chromatographic purification eluting with ethyl acetate-hexane (1:20) provided the subtitle compound (1.69 g. 67% yield) as a brown oil.

Workup

  1. temperaturethe resulting mixture was heated at 130° C. for 1.5 hours
  2. temperatureAfter cooling
  3. extractionThe whole was extracted with ethyl acetate-hexane (1:1, 200 mL×1, 100 mL×1)
  4. washthe combined organic layers washed with water, brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customChromatographic purification
  8. washeluting with ethyl acetate-hexane (1:20)

Sources & evidence

ORD record
ord-65a4f25cf6bf4d86a3530902dd7454e8
Source dataset
uspto-grants-2000_04
Patent number
US06048880

Reaction notes

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