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Cesium carbonate → Ethyl (3-{4-[(diphenylmethylene)amino]phenyl}cyclohexyl)acetate

HRID 1713846
ノート
印刷プレビュー

反応式

HRID 1713846 の反応式
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][CH2:16][CH:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14]2)=[CH:9][CH:8]=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[C:79](=[NH:92])([C:86]1[CH:91]=[CH:90][CH:89]=[CH:88][CH:87]=1)[C:80]1[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:80]1([C:79](=[N:92][C:7]2[CH:12]=[CH:11][C:10]([CH:13]3[CH2:18][CH2:17][CH2:16][CH:15]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14]3)=[CH:9][CH:8]=2)[C:86]2[CH:87]=[CH:88][CH:89]=[CH:90][CH:91]=2)[CH:85]=[CH:84][CH:83]=[CH:82][CH:81]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 59464250Ethyl [3-(4-{[(trifluoromethyl)sulphonyl]oxy}phenyl)cyclohexyl]acetate

生成物 1

HCID 59464258Ethyl (3-{4-[(diphenylmethylene)amino]phenyl}cyclohexyl)acetate収率 38%

試薬・触媒・溶媒 2

HCID 167845
palladium(II) acetate
触媒
HCID 8028Tetrahydrofuran溶媒

実験手順

Ethyl [3-(4-{[(trifluoromethyl)sulphonyl]oxy}phenyl)cyclohexyl]acetate (322 mg, 0.85 mmol) was stirred in dry THF (8 mL) under a nitrogen atmosphere and caesium carbonate (387 mg, 1.19 mmol), palladium(II) acetate (12 mg, 0.05 mmol) and BINAP (32 mg, 0.05 mmol) were added followed by benzophenone imine (0.214 mL, 1.27 mmol). The reaction vessel was degassed 6 times and stirred under reflux for 16 h. The mixture was extracted with ether (2×100 mL) and washed with water (100 mL). The organic extracts were dried and concentrated by evaporation to give an oil that was purified by chromatography eluting with 0-30% EtOAc/isohexane to give the title compound (137 mg, 38%) as an oil; 1H NMR δ 0.81-2.48 (m, 9H), 1.12-1.21 (m, 3H), 2.58-2.72 (m, 1H), 3.97-4.12 (m, 2H), 6.57-6.65 (m, 1H), 6.94-7.04 (m, 1H), 7.10-7.18 (m, 1H), 7.29-7.36 (m, 1H), 7.37-7.78 (m, 10H); MS m/e MH+ 426.

後処理

  1. customThe reaction vessel was degassed 6 times
  2. temperatureunder reflux for 16 h
  3. extractionThe mixture was extracted with ether (2×100 mL)
  4. washwashed with water (100 mL)
  5. customThe organic extracts were dried
  6. concentrationconcentrated by evaporation
  7. customto give an oil that
  8. customwas purified by chromatography
  9. washeluting with 0-30% EtOAc/isohexane

出典と根拠

ORDレコード
ord-0a90d8daa0af45c696388dce9fddc3fe
出典データセット
uspto-grants-2010_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07795283B2

反応ノート

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