Ammonium Chloride → methyl (4RS,6SR)-6-(3,4-dichlorophenyl)-6-hydroxy-2,4,-dimethylcyclohex-1-enecarboxylate

HRID 1891996Notes

Reaction equation

HRID 1891996 reaction equation
[CH3:1][C:2]1[CH2:7][CH:6]([CH3:8])[CH2:5][C:4](=[O:9])[C:3]=1[C:10]([O:12][CH3:13])=[O:11].[Cl:14][C:15]1[CH:16]=[C:17]([Mg]Br)[CH:18]=[CH:19][C:20]=1[Cl:21].[Cl-].[NH4+]>C1COCC1>[Cl:14][C:15]1[CH:16]=[C:17]([C:4]2([OH:9])[C:3]([C:10]([O:12][CH3:13])=[O:11])=[C:2]([CH3:1])[CH2:7][CH:6]([CH3:8])[CH2:5]2)[CH:18]=[CH:19][C:20]=1[Cl:21]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 67159275Methyl 2,4-dimethyl-6-oxocyclohex-1-enecarboxylateHCID 178478192HCID 178478192, compound

Product 1

HCID 131730802methyl (4RS,6SR)-6-(3,4-dichlorophenyl)-6-hydroxy-2,4,-dimethylcyclohex-1-enecarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of racemic methyl 2,4-dimethyl-6-oxocyclohex-1-enecarboxylate (Example 1-03, Step 4; 100 mg) in THF (5 mL) was treated with 3,4-dichlorophenylmagnesium bromide (0.5 M, 1.3 mL). The mixture was stirred at rt overnight and then treated with saturated aqueous ammonium chloride. The resulting mixture was extracted three times with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under vacuum to provide methyl (4RS,6SR)-6-(3,4-dichlorophenyl)-6-hydroxy-2,4,-dimethylcyclohex-1-enecarboxylate (97 mg). Mass spectrum m/z 353.32 (M+Na+).

Workup

  1. extractionThe resulting mixture was extracted three times with ethyl acetate
  2. washThe combined organic layers were washed with saturated aqueous sodium chloride
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-75c1370af87d4a87823a8dd705bb6e52
Source dataset
uspto-grants-2013_08
Patent number
US08507559B2

Reaction notes

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