Diethyl Ether → HCID 86754616, compound

HRID 1739734Notes

Reaction equation

HRID 1739734 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH3:10])=[C:4]([CH3:11])[C:3]=1[CH3:12].C([Li])(C)(C)C.FC(F)(F)S(O[C:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])(=O)=O.C(OCC)C>O1CCCC1.CCCCC.[Cl-].[Zn+2].[Cl-].[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:10][O:9][C:5]1[CH:6]=[C:7]([CH3:8])[C:2]([C:24]2[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=2[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[C:3]([CH3:12])[C:4]=1[CH3:11]

Participants

9

Reactant 4

HCID 3283Diethyl EtherHCID 394599Ethyl 2-[(trifluoromethanesulfonyl)oxy]cyclohex-1-ene-1-carboxylateHCID 14331811HCID 14331811, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 86754616HCID 86754616, compound

Reagents, catalysts & solvents 4

HCID 3007855ZincchlorideCatalystHCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred solution of 1-bromo-4-methoxy-2,3,6-trimethylbenzene in anhydrous tetrahydrofuran at -78° C. is added 1.7M tert-butyllithium in pentane, followed by the addition of zinc chloride, 0.5M in tetrahydrofuran. The mixture is allowed to warm to room temperature, tetrakis (triphenylphosphine) palladium(0) and ethyl 2-trifluoromethanesulfonyloxycyclohexen-1-ylcarboxylate in tetrahydrofuran is added and the resulting solution is stirred for 2 hours at the reflux temperature of the solvent. The reaction is cooled to room temperature, 50 ml of diethyl ether is added and the layers are separated. The organic layer is washed with water, aqueous sodium bicarbonate, saturated sodium chloride, and dried over sodium sulfate. Evaporation of the solution, followed by chromatography (silica gel: hexane/diethyl ether 4:1) gives 2-(4-methoxy-2,3,6-trimethylphenyl)-1-cyclohexene-1-carboxylic acid, ethyl ester.

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. customthe layers are separated
  3. washThe organic layer is washed with water, aqueous sodium bicarbonate, saturated sodium chloride
  4. dry with materialdried over sodium sulfate
  5. customEvaporation of the solution

Sources & evidence

ORD record
ord-36ce9dd23bc741069f8b74f76ab088da
Source dataset
uspto-grants-1999_10
Patent number
US05968908

Reaction notes

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