Toluene → 3-(2-Methoxyethoxymethyl-6-trifluoromethyl-pyridin-3-ylcarbonyloxy)-cyclohex-2-en-1-one

HRID 1784149Notes

Reaction equation

HRID 1784149 reaction equation
Cl[C:2]1[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=1.[CH3:9][O:10][CH2:11][CH2:12][O:13][CH2:14][C:15]1[N:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][C:16]=1[C:17]([OH:19])=[O:18].C1(C)C=CC=CC=1.C(N(C(C)C)CC)(C)C>[Cl-].[Cl-].[Zn+2].O.ClCCl>[CH3:9][O:10][CH2:11][CH2:12][O:13][CH2:14][C:15]1[C:16]([C:17]([O:19][C:2]2[CH2:7][CH2:6][CH2:5][C:4](=[O:8])[CH:3]=2)=[O:18])=[CH:20][CH:21]=[C:22]([C:24]([F:27])([F:25])[F:26])[N:23]=1

Participants

8

Reactant 4

HCID 1140Toluene2×HCID 81531DiisopropylethylamineHCID 5683453-Chlorocyclohex-2-en-1-oneHCID 113349532-(2-Methoxy-ethoxymethyl)-6-trifluoromethyl-nicotinic acid

Product 1

HCID 575915213-(2-Methoxyethoxymethyl-6-trifluoromethyl-pyridin-3-ylcarbonyloxy)-cyclohex-2-en-1-one

Reagents, catalysts & solvents 3

HCID 3007855ZincchlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 157 mg (1.15 mmol) of 3-chlorocyclohex-2-en-1-one, 16 mg (0.12 mmol) of ZnCl2, 324 mg (1.15 mmol) of 2-methoxyethoxymethyl-6-trifluoromethylnicotinic acid (preparation described in WO 2001094339) and 2 ml of toluene there are added dropwise, under a nitrogen atmosphere, over the course of 15 minutes, 166 mg (1.27 mmol) of diisopropylethylamine. A further 2 ml of toluene are then added and, with stirring, the reaction mixture is maintained under moderate reflux for 18 hours in an oil bath. The reaction mixture is then brought to ambient temperature and 30 ml of dichloromethane and 20 ml of water are added. The organic phase is separated off and washed twice with 0.1M hydrochloric acid (20 ml) and twice with water (10 ml). After drying using magnesium sulfate and concentration in vacuo, 226 mg of 3-(2-methoxyethoxymethyl-6-trifluoromethyl-pyridin-3-ylcarbonyloxy)-cyclohex-2-en-1-one are obtained in the form of an orange-brown oil.

Workup

  1. temperaturethe reaction mixture is maintained
  2. temperatureunder moderate reflux for 18 hours in an oil bath
  3. customis then brought to ambient temperature
  4. customThe organic phase is separated off
  5. washwashed twice with 0.1M hydrochloric acid (20 ml) and twice with water (10 ml)
  6. customAfter drying
  7. concentrationmagnesium sulfate and concentration in vacuo, 226 mg of 3-(2-methoxyethoxymethyl-6-trifluoromethyl-pyridin-3-ylcarbonyloxy)-cyclohex-2-en-1-one
  8. customare obtained in the form of an orange-brown oil

Sources & evidence

ORD record
ord-8a3c4571d07c44b796fe00511e454f86
Source dataset
uspto-grants-2009_03
Patent number
US07501544B2

Reaction notes

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