1,2-Dimethoxyethane → 2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-cyclopentane-1,3-dione

HRID 2170808Notes

Reaction equation

HRID 2170808 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([CH2:13]OC3CCC(=O)C=3)=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[N-](S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=[O:23].[CH2:36]([N+]1C=CN(C)C=1)[CH2:37][CH2:38][CH3:39].[CH3:46][O:47]CCOC>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([CH3:13])=[C:11]([CH:36]3[C:37](=[O:23])[CH2:38][CH2:39][C:46]3=[O:47])[N:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 669261233-[2-(4-Chloro-phenyl)-thiazol-5-ylmethoxy]-cyclopent-2-enoneHCID 1784485511-Butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide

Product 1

HCID 669260642-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-cyclopentane-1,3-dione

Conditions

Temperature
230 °C

Procedure

To a solution of 3-[2-(4-Chloro-phenyl)-thiazol-5-ylmethoxy]-cyclopent-2-enone (1.29 g, 4.22 mmol) in ethylene glycol dimethyl ether (10 ml) was added 1-butyl-3-methylimidazolium bis(trifluoromethylsulphonyl)imide (100 μl) and the reaction heated to 230° C. by microwave irradiation for 30 minutes. The crude reaction mixture was dry loaded onto silica and purified by flash chromatography to give 2-[2-(4-Chloro-phenyl)-5-methyl-thiazol-4-yl]-cyclopentane-1,3-dione (1.12 g).

Workup

  1. customThe crude reaction mixture
  2. customwas dry
  3. custompurified by flash chromatography

Sources & evidence

ORD record
ord-4c5cefa890dd4a6b8bd36502140c3197
Source dataset
uspto-grants-2015_06
Patent number
US09051300B2

Reaction notes

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