[4-Chloro-2-(2-chloro-phenoxy)-pyrimidin-5-yl]-thiophen-2-yl-methanol → [4-Chloro-2-(2-chloro-phenoxy)-pyrimidin-5-yl]-thiophen-2-yl-methanone

HRID 230162Notes

Reaction equation

HRID 230162 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)[OH:9])=[CH:6][N:5]=[C:4]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[N:3]=1>C1(C)C=CC=CC=1.O=[Mn]=O>[Cl:1][C:2]1[C:7]([C:8]([C:10]2[S:11][CH:12]=[CH:13][CH:14]=2)=[O:9])=[CH:6][N:5]=[C:4]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[Cl:22])[N:3]=1

Participants

4

Reactant 1

HCID 59834363[4-Chloro-2-(2-chloro-phenoxy)-pyrimidin-5-yl]-thiophen-2-yl-methanol

Product 1

HCID 59834304[4-Chloro-2-(2-chloro-phenoxy)-pyrimidin-5-yl]-thiophen-2-yl-methanone

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 1140TolueneSolvent

Procedure

[4-Chloro-2-(2-chloro-phenoxy)-pyrimidin-5-yl]-thiophen-2-yl-methanol (98 mg, 0.28 mmol)was dissolved in 15 mL dry toluene, and 250 mg of MnO2 was added. The reaction mixture was heated to reflux for 30 minutes, and water was removed using a Dean Stark apparatus. The hot reaction mixture was filtered through Celite, and the Celite was washed five times with 3.5 mL of hot EtOAc. The combined organics were evaporated under reduced pressure to yiled 82 mg of [4-Chloro-2-(2-chloro-phenoxy)-pyrimidin-5-yl]-thiophen-2-yl-methanone as an oil. Mass Spec. M+H=352.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 30 minutes
  3. customwater was removed
  4. filtrationThe hot reaction mixture was filtered through Celite
  5. washthe Celite was washed five times with 3.5 mL of hot EtOAc
  6. customThe combined organics were evaporated under reduced pressure to yiled 82 mg of [4-Chloro-2-(2-chloro-phenoxy)-pyrimidin-5-yl]-thiophen-2-yl-methanone as an oil

Sources & evidence

ORD record
ord-5e1f49e4c4f6459eafe9e32944cc759b
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

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