Ammonium Chloride → HCID 45096823, compound

HRID 12054Notes

Reaction equation

HRID 12054 reaction equation
[Cl-].[Li+].[CH3:3][C:4]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:16])[CH:5]=1.[CH3:17][Mg]Br.[Cl-].[NH4+]>O1CCCC1.[Cu](I)I>[CH3:3][C:4]1([CH3:17])[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][C:6](=[O:16])[CH2:5]1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2383403-methyl-4-phenylcyclohex-2-en-1-oneHCID 433294Lithium ChlorideHCID 178418573HCID 178418573, compound

Product 1

HCID 45096823HCID 45096823, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium chloride (0.6 mmol) and copper iodide (0.3 mmol) are introduced first under argon in dry tetrahydrofuran (18 ml). At 0° C. 3-methyl-4-phenylcyclohex-2-enone (3 mmol) is added and stirring continues for another 10 min at this temperature. Then a solution of methylmagnesium bromide (3.6 mmol) is slowly added dropwise and the reaction mixture is maintained at 0° C. for 3 hours accompanied by stirring. The reaction is stopped by adding saturated aqueous ammonium chloride solution. The mixture is extracted with diethyl ether. The title compound is obtained from the combined organic phases after drying over sodium sulphate and evaporating-off of the solvent in a vacuum (J. Organom. Chem. 1995, 502, C5-C7): tR 2.36 min (LC-2); ESI-MS (+): m/z 203.35 [M+H]+.

Workup

  1. customAt 0° C
  2. stirringby stirring
  3. extractionThe mixture is extracted with diethyl ether

Sources & evidence

ORD record
ord-471a2517555541d38d29395f8a35a9fa
Source dataset
uspto-grants-2010_06
Patent number
US07727979B2

Reaction notes

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