Potassium Carbonate → Methyl 7-(4-methoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate

HRID 566077ノート

反応式

HRID 566077 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[S: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:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.O>[CH3:26][O:25][C:22]1[CH:23]=[CH:24][C:19]([C:2]2[CH:3]=[CH:4][C:5]3[S: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][CH:21]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 18472606HCID 18472606、化合物HCID 86645335(4-Methoxyphenyl)borate

生成物 1

HCID 18472336Methyl 7-(4-methoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate収率 85.5%

試薬・触媒・溶媒 1

HCID 86587398Ethanol toluene water溶媒

実験手順

Under argon atmosphere, a mixture of methyl 7-bromo-2,3-dihydro-1-benzothiepine-4-carboxylate (1.5 g), 4-methoxyphenyl borate (0.84 g) and potassium carbonate (1.39 g) in toluene/ethanol/water (50/5/5 ml) was stirred at room temperature for 1 hour. To the mixture was added tetrakistriphenylphosphine palladium (0.17 g), and the mixture was refluxed for 24 hours and then cooled. The mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the mixture was concentrated, and the residue was purified with column chromatography (ethyl acetate/hexane=1:15→1:9→1:4→1:2) to give pale yellow crystals of methyl 7-(4-methoxyphenyl)-2,3-dihydro-1-benzothiepine-4-carboxylate (1.40 g).

後処理

  1. temperaturethe mixture was refluxed for 24 hours
  2. temperaturecooled
  3. extractionThe mixture was extracted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationUnder reduced pressure, the mixture was concentrated
  7. customthe residue was purified with column chromatography (ethyl acetate/hexane=1:15→1:9→1:4→1:2)

出典と根拠

ORDレコード
ord-ad9fa92ca3e04b928532c246fc187d7a
出典データセット
uspto-grants-2001_01
特許番号
US06172061B2

反応ノート

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