Methyl iodide → 3-Methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one

HRID 2299652Notes

Reaction equation

HRID 2299652 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1.[C:14](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O.C(OCC)(=O)C>[CH3:14][O:1][C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2295073-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one

Product 1

HCID 133574413-Methoxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-oneYield 72.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
52.5 °C

Procedure

A mixture of 3-hydroxy-6,7,8,9-tetrahydrobenzocyclohepten-5-one (7.02 g), potassium carbonate (8.25 g) and iodomethane (7.4 ml) in N,N-dimethylformamide (70 ml) was stirred at 50-55° C. for 7 hours. The resulting mixture was diluted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo to afford 3-methoxy-6,7,8,9-tetrahydrobenzocyclohepten-5-one (5.49 g).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-3d383ff086c34447b9c342bf18c762a5
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

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