Phenol → HCID 178426798, compound

HRID 1385298Notes

Reaction equation

HRID 1385298 reaction equation
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:8][C:9]1([CH3:28])[CH2:26][C:13]2=[C:14]([C:21]3[CH:25]=[CH:24][NH:23][N:22]=3)[S:15][C:16](S(C)(=O)=O)=[C:12]2[C:11](=[O:27])[CH2:10]1.[OH-].[Na+]>C1COCC1.CCOC(C)=O>[CH3:8][C:9]1([CH3:28])[CH2:26][C:13]2=[C:14]([C:21]3[CH:25]=[CH:24][NH:23][N:22]=3)[S:15][C:16]([O:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[C:12]2[C:11](=[O:27])[CH2:10]1

Participants

6

Reactant 3

HCID 996Phenol2×HCID 14798Sodium Hydroxide2×HCID 178426801HCID 178426801, compound

Product 1

HCID 178426798HCID 178426798, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of phenol (116 mg, 1.1 mmol) in THF (10 mL) was added 6,6-dimethyl-3-methanesulphonyl-1-(pyrazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (0.2 g, 0.62 mmol) and NaOH (0.3 mL of a 4M solution, 1.1 mmol). The mixture was heated at reflux overnight. Phenol (50 mg, 0.62 mmol) and NaOH (0.15 mL of a 4M solution, 0.62 mmol) were then added and the mixture heated at reflux for an additional 8 h. The solution was cooled to room temperature, diluted with EtOAc (100 mL) and washed with NaOH (1M, 2×100 mL). The organic layer was separated, dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with hexane:EtOAc (2:1) to give the title compound (35 mg, 18%) as a yellow solid. mp 232-234° C. 1H NMR (360 MHz, CDCl3) δ 1.10 (6H, s), 2.42 (2H, s), 2.86 (2H, s), 6.43 (1H, d, J=2.3 Hz), 7.20-7.26 (3H, m), 7.37 (1H, d, J=7.3 Hz), 7.39 (1H, d, J=8.7 Hz), 7.59 (1H, d, J=2.3 Hz). MS (ES+) 339 (M+1).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperaturethe mixture heated
  4. temperatureat reflux for an additional 8 h
  5. washwashed with NaOH (1M, 2×100 mL)
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customThe residue was chromatographed on silica gel
  10. washeluting with hexane:EtOAc (2:1)

Sources & evidence

ORD record
ord-acadb85e5cd741dca97bea4ee156f494
Source dataset
uspto-grants-2001_07
Patent number
US06262103B1

Reaction notes

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