Water → 2-Methoxy-5-(3,4,5-trimethoxyphenyl)-6,7,8,9-tetrahydro-benzocyclohepten-5-ol

HRID 1944632

Reaction equation

HRID 1944632 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](Br)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C([Li])CCC.[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]2[C:30](=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=2[CH:32]=1.O>CCOCC>[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]2[C:30]([C:5]3[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=3)([OH:31])[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=2[CH:32]=1

Participants

6

Reactant 4

HCID 962WaterHCID 758855-Bromo-1,2,3-trimethoxybenzeneHCID 2668152-Methoxy-6,7,8,9-tetrahydro-benzocyclohepten-5-oneHCID 178418339Butyllithium

Product 1

HCID 689233112-Methoxy-5-(3,4,5-trimethoxyphenyl)-6,7,8,9-tetrahydro-benzocyclohepten-5-olYield 49.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-30 °C

Procedure

200 mL of anhydrous ether was, added to 3,4,5-trimethoxybromobenzene (1.23 g, 4.97 mmol) in a 500 mL round bottom flask under nitrogen. The temperature of the reaction mixture was brought to −78° C. n-Butyllithium (4.5 mL, 11.25 mmol) was added dropwise. The reaction mixture was then stirred until the temperature was raised gradually to −30° C. 30 (0.86 g, 4.5 mmol) dissolved in 25 mL of dry ether was added dropwise and the reaction mixture was allowed to stir until the temperature warmed up to room temperature. 25 mL of water was added and the product was extracted with ether (3×50), combined organic phases were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. Purification by column chromatography (silica gel, 20:80 EtOAc:Hexanes) yielded 800 mg (49%) of 32 as pale yellow oil Rf: 0.16 (30:70, EtOAc:Hexanes).

Workup

  1. customwas brought to −78° C.
  2. additionwas added dropwise
  3. additionwas added dropwise
  4. stirringto stir until the temperature
  5. temperaturewarmed up to room temperature
  6. extractionthe product was extracted with ether (3×50)
  7. dry with materialwere dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure
  10. customPurification by column chromatography (silica gel, 20:80 EtOAc:Hexanes)

Sources & evidence

ORD record
ord-7e856409b24c4f438c561ad63c878ccd
Source dataset
uspto-grants-2013_03
Patent number
US08394859B2

Linked notes

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