Potassium Carbonate → HCID 22990055, compound

HRID 1169333Notes

Reaction equation

HRID 1169333 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[F:23][C:24]([F:38])([F:37])[C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:32]=1)[CH2:28]Br>CN(C=O)C>[F:23][C:24]([F:37])([F:38])[C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([C:33]([F:36])([F:34])[F:35])[CH:32]=1)[CH2:28][O:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1225733,5-Bis(trifluoromethyl)benzyl bromideHCID 22989944methyl 2-hydroxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate

Product 1

HCID 22990055HCID 22990055, compoundYield 81.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To methyl 2-hydroxy-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (327 mg, 1.50 mmol) dissolved in DMF (6 ml) were added potassium carbonate (415 mg, 3.00 mmol) and 3,5-bis(trifluoromethyl)benzyl bromide (302 mg, 1.65 mmol), and the resulting mixture was stirred at room temperature for 17 hours. The reaction mixture was concentrated under reduced pressure, ethyl acetate (40 ml) was added to the residue and the resulting mixture was washed with water (5 ml×2) and an aqueous saturated solution of sodium chloride (5 ml). The organic layer was dried with anhydrous magnesium sulfate and was then concentrated under reduced pressure, and the residue was subjected to column chromatography (silica gel: 15 g, ethyl acetate/hexane=1/25). The objective fractions were concentrated under reduced pressure, hexane was added to the residue and an insoluble material was collected by filtration. The insoluble material was washed with hexane and was then dried under reduced pressure to obtain methyl 2-[3,5-bis(trifluoromethyl)benzyloxy]-6,7-dihydro-5H-benzocycloheptene-8-carboxylate (524 mg, 1.22 mmol, 81%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate (40 ml)
  2. additionwas added to the residue
  3. washthe resulting mixture was washed with water (5 ml×2)
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. concentrationwas then concentrated under reduced pressure
  6. concentrationThe objective fractions were concentrated under reduced pressure, hexane
  7. additionwas added to the residue
  8. filtrationan insoluble material was collected by filtration
  9. washThe insoluble material was washed with hexane
  10. customwas then dried under reduced pressure

Sources & evidence

ORD record
ord-f51f7b19fbfa4276aedb492a3d304e2d
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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