p-Anisyl thiophen-2-yl ketone → 4-(Thiophene-2-carbonyl)phenol

HRID 1857126Notes

Reaction equation

HRID 1857126 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:13]=[CH:12][C:11]([O:14]C)=[CH:10][CH:9]=1)=[O:7].C[S-].[Na+]>CN(C)C=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1)=[O:7]

Participants

4

Reactant 2

HCID 77812p-Anisyl thiophen-2-yl ketoneHCID 4378561Sodium methanethiolate

Product 1

HCID 130205054-(Thiophene-2-carbonyl)phenolYield 93.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Methoxyphenyl 2-thienyl ketone (804 mg) obtained in Example 38 was dissolved in N,N-dimethylformamide (30 ml), sodium thiomethoxide (645 mg) was added, and the admixture was refluxed under argon for 5 hours. The reaction mixture was partitioned in the same manner as described in Example 33. The ethyl acetate layer was dried with anhydrous magnesium sulfate, the solvent was removed by reduced-pressure distillation, and the resulting residue was purified by column chromatography on silica gel eluting with chloroform to obtain 702 mg of the title compound (yield: 93%).

Workup

  1. temperaturethe admixture was refluxed under argon for 5 hours
  2. customThe reaction mixture was partitioned in the same manner
  3. dry with materialThe ethyl acetate layer was dried with anhydrous magnesium sulfate
  4. customthe solvent was removed by reduced-pressure distillation
  5. customthe resulting residue was purified by column chromatography on silica gel eluting with chloroform

Sources & evidence

ORD record
ord-27bc688160e54f4ab4619273933be1a4
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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