Tetrahydrofuran → HCID 67158615, compound

HRID 1891987Notes

Reaction equation

HRID 1891987 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([Mg]Br)[CH:5]=[CH:6][C:7]=1[Cl:8].C[CH:12]1[CH2:17][CH2:16][C:15](=O)[C:14]([C:19]([OH:21])=[O:20])=[C:13]1[CH3:22].[Cl-].[NH4+].[CH2:25]1COCC1>[Cu]Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]2[CH2:16][CH2:17][CH2:12][CH:13]([CH3:22])[CH:14]2[C:19]([O:21][CH3:25])=[O:20])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 25517Ammonium ChlorideHCID 67158422HCID 67158422, compoundHCID 178478192HCID 178478192, compound

Product 1

HCID 67158615HCID 67158615, compound

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Conditions

Temperature
0 °C

Procedure

A suspension of copper (I) chloride (164 mg) in THF (4 mL) was stirred at 0° C. and treated with 3,4-dichlorophenylmagnesium bromide (0.5 M in THF, 3.3 mL). The mixture was stirred for 5 min, then was treated with a solution of methyl 2-methyl-6-oxocyclohex-1-enecarboxylic acid (prepared according to the procedure of Belmont, D. T. et al., J. Org. Chem. 1985, 50, 4102; 140 mg) in THF. The mixture was allowed to warm to rt over 30 min, then was cooled to 0° C. and treated with a 9:1 solution of saturated ammonium chloride-concentrated ammonium hydroxide. The mixture was extracted three times with ethyl acetate and the combined organic layers were washed with saturated aqueous ammonium chloride, dried over sodium sulfate and then concentrated under vacuum. The resulting residue was filtered through silica gel to provide methyl 2-(3,4-dichlorophenyl)-6-methylcyclohexanecarboxylate (153 mg). Mass spectrum m/z 316.44 (M+H+).

Workup

  1. stirringThe mixture was stirred for 5 min
  2. customprepared
  3. temperatureto warm to rt over 30 min
  4. temperaturewas cooled to 0° C.
  5. extractionThe mixture was extracted three times with ethyl acetate
  6. washthe combined organic layers were washed with saturated aqueous ammonium chloride
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under vacuum
  9. filtrationThe resulting residue was filtered through silica gel

Sources & evidence

ORD record
ord-9c06eb5caae44371a9d65eb825e3890d
Source dataset
uspto-grants-2013_08
Patent number
US08507559B2

Reaction notes

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