Cesium carbonate → HCID 66653950、化合物

HRID 571778ノート

反応式

HRID 571778 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[OH:9].[H-].[Na+].[CH2:12]([N:19]1[CH2:24][CH2:23][O:22][CH:21]([C:25]2[CH:30]=[CH:29][C:28](Br)=[CH:27][CH:26]=2)[CH2:20]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CC(C)(C(=O)CC(=O)C(C)(C)C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.[Cu]I>[CH2:12]([N:19]1[CH2:24][CH2:23][O:22][CH:21]([C:25]2[CH:30]=[CH:29][C:28]([O:9][C:3]3[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])=[CH:27][CH:26]=2)[CH2:20]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

8

反応物 5

HCID 10796Cesium carbonateHCID 113352,6-DimethylphenolHCID 24758Sodium hydrideHCID 707002,2,6,6-Tetramethyl-3,5-heptanedioneHCID 580978794-Benzyl-2-(4-bromo-phenyl)-morpholine

生成物 1

HCID 66653950HCID 66653950、化合物

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 1140Toluene溶媒2 回

実験手順

2,6-Dimethylphenol was added portionwise to a suspension of NaH (272 mg, 60% in oil, 6.8 mmol) in toluene (15 mL). After complete addition the mixture was heated under reflux for 15 min. and subsequently cooled to room temperature. To the resulting mixture was added a solution of 4-benzyl-2-(4-bromo-phenyl)-morpholine (1.5 g, 4.5 mmol) in toluene (10 mL), followed by copper(I) iodide (438 mg, 2.3 mmol), 2,2,6,6-tetramethyl-3,5-heptanedione (0.48 mL, 2.3 mmol), and cesium carbonate (2.96 g, 9.1 mmol). The obtained mixture was heated under reflux for 3 days. After cooling to room temperature, the mixture was partitioned between EtOAc and water. The layers were separated. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (EtOAc:heptanes 5:95) to afford 4-benzyl-2-[4-(2,6-dimethyl-phenoxy)-phenyl]-morpholine (1.2 g), which was used as such in the next step.

後処理

  1. additionAfter complete addition the mixture
  2. temperaturewas heated
  3. temperatureunder reflux for 15 min.
  4. temperatureThe obtained mixture was heated
  5. temperatureunder reflux for 3 days
  6. temperatureAfter cooling to room temperature
  7. customthe mixture was partitioned between EtOAc and water
  8. customThe layers were separated
  9. dry with materialThe organic layer was dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customThe residue was purified by column chromatography (EtOAc:heptanes 5:95)

出典と根拠

ORDレコード
ord-9c21d0fe4ee74519a074e5fad5331fed
出典データセット
uspto-grants-2015_05
特許番号
US09029371B2

反応ノート

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