Methanol → HCID 14127257, compound

HRID 1651436Notes

Reaction equation

HRID 1651436 reaction equation
Cl[C:2]1(Cl)[CH:9]2[CH:4]([CH2:5][CH2:6][CH:7]=[CH:8]2)[C:3]1=[O:10].C(N(CC)CC)C.[Cl-].[NH4+].[CH3:21][OH:22]>[Cu].[Zn]>[CH3:21][O:22][C:4]12[C:3](=[O:10])[CH2:2][CH:9]1[CH:8]=[CH:7][CH2:6][CH2:5]2

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 125073478,8-Dichlorobicyclo[4.2.0]oct-2-en-7-one

Product 1

HCID 14127257HCID 14127257, compound

Reagents, catalysts & solvents 1

HCID 10290809Zinc copper coupleCatalyst

Procedure

To a stirred solution of 60 g of 8,8-dichlorobicyclo[4.2.0]oct-2-en-7-one, prepared as shown in Preparation 1, in 500 ml of methanol under nitrogen at room temperature was added 48 ml of triethylamine over a period of 1 hour. The mixture was stirred for 30 minutes, then 90 g of ammonium chloride and 60 g of zinc-copper couple (as a powder) was added. The reaction mixture was stirred at room temperature for 2.5 hours, filtered through Celite and the solvent removed under reduced pressure. The residue was dissolved in ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and the solvent was distilled under vacuum, giving 32 g of 6-methoxybicyclo[4.2.0]oct-2-en-7-one.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 2.5 hours
  2. filtrationfiltered through Celite
  3. customthe solvent removed under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled under vacuum

Sources & evidence

ORD record
ord-f342b78bf96749d780cdea7da8d53ce3
Source dataset
uspto-grants-1990_05
Patent number
US04927963

Reaction notes

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