Sodium Carbonate → 2-(3-Methoxyphenyl)-6,7-dihydro-5H-benzo[b]thiophen-4-one

HRID 2063746ノート

反応式

HRID 2063746 の反応式
Br[C:2]1[S:6][C:5]2[CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1.B(O)O.[CH3:15][O:16][C:17]1[CH:18]=[C:19](O)[CH:20]=[CH:21][CH:22]=1.C([O-])([O-])=O.[Na+].[Na+].CCO.O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[CH3:15][O:16][C:17]1[CH:22]=[C:21]([C:2]2[S:6][C:5]3[CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=3[CH:3]=2)[CH:20]=[CH:19][CH:18]=1

参加物

7

反応物 4

HCID 10340Sodium CarbonateHCID 6160702-Bromo-4,5,6,7-tetrahydro-1-benzothiophen-4-oneHCID 19096565Water ethanolHCID 178491272HCID 178491272、化合物

生成物 1

HCID 592628582-(3-Methoxyphenyl)-6,7-dihydro-5H-benzo[b]thiophen-4-one収率 95%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

To 2-bromo-6,7-dihydro-5H-benzo[b]thiophen-4-one (5 g, 21.74 mmol) was successively added 3-methoxyphenol boronic acid (3.63 g, 23.92 mmol), 2M Na2CO3(aq) (43.5 mL, 86.98 mmol), Pd(PPh3)4 (251 mg, 0.22 mmol), 3:4 EtOH/H2O (37.5 mL) and DME (62.5 mL). The reaction mixture was degassed and heated to reflux for 12 hours. EtOAc (250 mL) was added and the crude reaction mixture was washed with water (2×100 mL). The organic layer was dried over magnesium sulphate, filtered and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with EtOAc:hexanes (20:80) to give the title compound as an off-white solid in 95% yield. MS (ES+) 259. δH (d6 DMSO) 2.13 (2H, quint.), 2.50 (2H, m), 3.05 (2H, t), 3.81 (3H, s), 6.91 (1H, m), 7.20-7.22 (2H, m), 7.34 (1H, m), 7.67 (1H, s).

後処理

  1. customThe reaction mixture was degassed
  2. temperatureheated
  3. temperatureto reflux for 12 hours
  4. additionEtOAc (250 mL) was added
  5. customthe crude reaction mixture
  6. washwas washed with water (2×100 mL)
  7. dry with materialThe organic layer was dried over magnesium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel chromatography
  11. washeluting with EtOAc:hexanes (20:80)

出典と根拠

ORDレコード
ord-4bf61ec677af46e78cc65ca38e0e4ccb
出典データセット
uspto-grants-2012_10
特許番号
US08288400B2

反応ノート

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