Dimethyl Carbonate → methyl 5-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulene-6-carboxylate

HRID 1014930Notes

Reaction equation

HRID 1014930 reaction equation
[H-].[Na+].[CH2:3]1[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6](=[O:7])[CH2:5][CH2:4]1.[C:15](=O)([O:18]C)[O:16][CH3:17]>>[O:7]=[C:6]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[CH2:14][CH2:3][CH2:4][CH:5]1[C:15]([O:16][CH3:17])=[O:18]

Participants

4

Reactant 3

HCID 12021Dimethyl Carbonate2×HCID 24758Sodium hydrideHCID 70003Benzosuberone

Product 1

HCID 10104791methyl 5-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulene-6-carboxylate

Conditions

Temperature
85 °C

Procedure

A solution of dimethyl carbonate (20 mL) was treated with NaH (3 g, 60% dispersed in oil, 75 mmol) and heated to 85° C. To the mixture was dropwise added a solution of bezosuberone (3 g, 18.75 mmol) in dimethyl carbonate (10 mL). The resulting mixture was refluxed for 3 hours, cooled to 0° C., quenched with HCl (1N) (100 mL) and extracted with ether. The organic layer was washed with NaHCO3 and brine, dried (MgSO4) and concentrated to provide the title compound as a brownish oil.

Workup

  1. temperatureThe resulting mixture was refluxed for 3 hours
  2. temperaturecooled to 0° C.
  3. customquenched with HCl (1N) (100 mL)
  4. extractionextracted with ether
  5. washThe organic layer was washed with NaHCO3 and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a965cdfe319f4acb9beef2b7aecfffe0
Source dataset
uspto-grants-2011_07
Patent number
US07985745B2

Reaction notes

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