Potassium Carbonate → Methyl 7-(5-methyl-2-thienyl)-2,3-dihydro-1-benzoxepine-4-carboxylate

HRID 1277263ノート

反応式

HRID 1277263 の反応式
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[S:20][C:21]([CH3:24])=[CH:22][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O>[CH3:24][C:21]1[S:20][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:23][CH:22]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 22990005Methyl 7-bromo-2,3-dihydro-1-benzooxepine-4-carboxylateHCID 867561815-Methyl-2-thienyl borate

生成物 1

HCID 18472362Methyl 7-(5-methyl-2-thienyl)-2,3-dihydro-1-benzoxepine-4-carboxylate収率 58.1%

試薬・触媒・溶媒 1

HCID 86587398Ethanol toluene water溶媒

実験手順

In toluene/ethanol/water (10/1/1) (24 ml) was dissolved methyl 7-bromo-2,3-dihydro-1-benzoxepine-4-carboxylate (560 mg), and to the mixture were added 5-methyl-2-thienyl borate (875 mg) and potassium carbonate (1.56 g). The mixture was stirred at room temperature for 30 minutes. To the mixture was added tetrakistriphenylphosphine palladium (260 mg), and the mixture was stirred at 100° C. for 24 hours and cooled to room temperature. 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=12/1) to give methyl 7-(5-methyl-2-thienyl)-2,3-dihydro-1-benzoxepine-4-carboxylate (345 mg).

後処理

  1. stirringthe mixture was stirred at 100° C. for 24 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=12/1)

出典と根拠

ORDレコード
ord-a292897a6fd44459994577ffd419a695
出典データセット
uspto-grants-2000_12
特許番号
US06166006

反応ノート

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