Potassium Carbonate → Methyl 7-(3-thienyl)-2,3-dihydro-1-benzoxepine-4-carboxylate

HRID 1277265Notes

Reaction equation

HRID 1277265 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=2[CH:16]=1.B([O-])([O-])O[C:19]1[CH:23]=[CH:22][S:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O>[S:21]1[CH:22]=[CH:23][C:19]([C:2]2[CH:3]=[CH:4][C:5]3[O:11][CH2:10][CH2:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][C:6]=3[CH:16]=2)=[CH:20]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 22990005Methyl 7-bromo-2,3-dihydro-1-benzooxepine-4-carboxylateHCID 867561823-Thienyl borate

Product 1

HCID 18472510Methyl 7-(3-thienyl)-2,3-dihydro-1-benzoxepine-4-carboxylateYield 86.2%

Reagents, catalysts & solvents 1

HCID 86587398Ethanol toluene waterSolvent

Procedure

In toluene/ethanol/water (10/1/1) (12 ml) was dissolved methyl 7-bromo-2,3-dihydro-1-benzoxepine-4-carboxylate (700 mg), and to the mixture were added 3-thienyl borate (422 mg) and potassium carbonate (0.98 g). The mixture was stirred at room temperature for 30 minutes, and to the mixture was added tetrakistriphenylphosphine palladium (136 mg). The mixture was stirred at 100° C. for 13 hours and cooled to room temperature, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was removed, and the resulting residue was purified with silica gel column chromatography (hexane/acetone=3/1) to give methyl 7-(3-thienyl)-2,3-dihydro-1-benzoxepine-4-carboxylate (610 mg).

Workup

  1. stirringThe mixture was stirred at 100° C. for 13 hours
  2. temperaturecooled to room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. customUnder reduced pressure, the solvent was removed
  7. customthe resulting residue was purified with silica gel column chromatography (hexane/acetone=3/1)

Sources & evidence

ORD record
ord-2d1c39779e6644b181238c1198fdc4f2
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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