Water → 4-(4-chlorophenyl)-4-hydroxy-2-pyridin-4-yl-4,5,6,7-tetrahydro-8H-cyclohepta[b]thiophen-8-one

HRID 1615521Notes

Reaction equation

HRID 1615521 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:24])[C:17]3[CH:16]=[C:15]([C:18]4[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=4)[S:14][C:13]=3[CH2:12][CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[O:25]1CCOCC1.C(#N)C.O.S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+]>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:24])[C:17]3[CH:16]=[C:15]([C:18]4[CH:19]=[CH:20][N:21]=[CH:22][CH:23]=4)[S:14][C:13]=3[C:12](=[O:25])[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 24412Potassium PersulfateHCID 312751,4-DioxaneHCID 681831404-(4-chlorophenyl)-2-pyridin-4-yl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-4-ol

Product 1

HCID 681832574-(4-chlorophenyl)-4-hydroxy-2-pyridin-4-yl-4,5,6,7-tetrahydro-8H-cyclohepta[b]thiophen-8-one

Reagents, catalysts & solvents 1

HCID 24463Copper sulfate pentahydrateCatalyst

Conditions

Temperature
90 °C

Procedure

To a solution of 4-(4-chlorophenyl)-2-pyridin-4-yl-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-4-ol (46.3 mg, 0.130 mmol) in 1,4-dioxane (3.0 mL, 38.0 mmol), acetonitrile (3.0 mL, 57 mmol) and water (2 mL, 100 mmol) were added copper(II) sulfate pentahydrate (145.0 mg, 0.580 mmol) and potassium persulfate (180.0 mg, 0.666 mmol). The reaction mixture was stirred for 16 hr at 90° C. during which time a yellow-greenish suspension was obtained and the blue color of the reaction disappeared.

Workup

  1. customwas obtained

Sources & evidence

ORD record
ord-87e6fb6d874546829cebbaf58a649d61
Source dataset
uspto-grants-2014_07
Patent number
US08765746B2

Reaction notes

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