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

HRID 33951Notes

Reaction equation

HRID 33951 reaction equation
[CH:1]([O:4][C:5]1[C:10]2[CH2:11][CH2:12][CH2:13][C:14]([C:17]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=3)(O)[CH2:15][C:9]=2[CH:8]=[CH:7][C:6]=1[O:29][CH3:30])([CH3:3])[CH3:2]>C(O)(=O)C.O>[CH:1]([O:4][C:5]1[C:10]2[CH2:11][CH2:12][CH2:13][C:14]([C:17]3[CH:22]=[C:21]([O:23][CH3:24])[C:20]([O:25][CH3:26])=[C:19]([O:27][CH3:28])[CH:18]=3)=[CH:15][C:9]=2[CH:8]=[CH:7][C:6]=1[O:29][CH3:30])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 689229651-Isopropoxy-2-methoxy-6-(3,4,5-trimethoxy-phenyl)-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-ol

Product 1

HCID 689232404-Isopropoxy-3-methoxy-8-(3,4,5-trimethoxy-phenyl)-6,7-dihydro-5H-benzocyclohepteneYield 95.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of the SM (40) (1.1 g, 2.64 mmol) in 30 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 ethylacetate:hexanes), to afford 1 g (95%) of 4-Isopropoxy-3-methoxy-8-(3,4,5-trimethoxy-phenyl)-6,7-dihydro-5H-benzocycloheptene as white crystals. Rf:56 (60:40, Hex:EA)

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 ethylacetate:hexanes)

Sources & evidence

ORD record
ord-01a378ce1f094fe99287709cc07fb4f3
Source dataset
uspto-grants-2008_09
Patent number
US07429681B2

Reaction notes

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