2-Methoxy-5-(3,4,5-trimethoxyphenyl)-6,7,8,9-tetrahydro-benzocyclohepten-5-ol → 3-Methoxy-9-(3,4,5-trimethoxy-phenyl)-6,7-dihydro-5H-benzocycloheptene

HRID 1944633Notes

Reaction equation

HRID 1944633 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]([C:14]3[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=3)(O)[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:26]=1>C(O)(=O)C.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:12]([C:14]3[CH:15]=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=3)=[CH:11][CH2:10][CH2:9][CH2:8][C:7]=2[CH:26]=1

Participants

4

Reactant 1

HCID 689233112-Methoxy-5-(3,4,5-trimethoxyphenyl)-6,7,8,9-tetrahydro-benzocyclohepten-5-ol

Product 1

HCID 159861643-Methoxy-9-(3,4,5-trimethoxy-phenyl)-6,7-dihydro-5H-benzocyclohepteneYield 91%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of the 32 (800 mg, 2.23 mmol) in 20 mL of acetic acid and 100 mL of water, taken in a 250 mL round bottom flask were refluxed for 12 h. The reaction mixture was cooled and extracted with dichloromethane (3×25 mL) and the combined organic phases were dried over magnesium sulfate. The solvent evaporated and the crude product was purified by flash column chromatography (10:90 EtOAc:Hexanes), to afford 690 mg (91%) of 2 as white crystals. Rf: 0.43 (30:70, EtOAc:Hexanes).

Workup

  1. customtaken in a 250 mL round bottom flask
  2. temperaturewere refluxed for 12 h
  3. temperatureThe reaction mixture was cooled
  4. extractionextracted with dichloromethane (3×25 mL)
  5. dry with materialthe combined organic phases were dried over magnesium sulfate
  6. customThe solvent evaporated
  7. customthe crude product was purified by flash column chromatography (10:90 EtOAc:Hexanes)

Sources & evidence

ORD record
ord-9e21d0d84f74468dbff0d286ec4983d9
Source dataset
uspto-grants-2013_03
Patent number
US08394859B2

Reaction notes

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