Triethylamine → 4-Methoxy-2',4',6'-tri-iso-propylbiphenyl

HRID 1627961Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1627961
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[CH:12]([C:15]1[CH:20]=[C:19]([CH:21]([CH3:23])[CH3:22])[CH:18]=[C:17]([CH:24]([CH3:26])[CH3:25])[CH:16]=1)([CH3:14])[CH3:13].CCN(CC)CC>O.[Cl-].[Na+].O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:20]2[C:15]([CH:12]([CH3:13])[CH3:14])=[CH:16][C:17]([CH:24]([CH3:26])[CH3:25])=[CH:18][C:19]=2[CH:21]([CH3:23])[CH3:22])=[CH:5][CH:4]=1

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 128601,3,5-TriisopropylbenzeneHCID 201262(4-Methoxyphenyl)boronic acid

Produkt 1

HCID 154676664-Methoxy-2',4',6'-tri-iso-propylbiphenylAusbeute 88,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

4-Methoxyphenylboronic acid (152 mg, 1.00 mmol), and Pd(dtbpf)Cl2 (6 mg, 0.01 mmol) were added to a reaction tube equipped with a magnetic stir bar. Under a positive flow of argon while stirring, surfactant solution (1.0 mL, 2 wt % TPGS-M-PEG-750 in water), 2,4,6-triisopropylbenzene (126 μL, 0.50 mmol), and Et3N (0.21 mL, 1.5 mmol) were added by syringe and stirred vigorously for 24 h. The reaction mixture was then diluted with brine and extracted with EtOAc. The solution obtained was dried over MgSO4 and concentrated by rotary evaporation. The residue was purified by flash column chromatography eluting with 5% CH2Cl2/hexanes to afford the product (137 mg, 88%) as a white solid.

Aufarbeitung

  1. customequipped with a magnetic stir bar
  2. stirringstirred vigorously for 24 h
  3. extractionextracted with EtOAc
  4. customThe solution obtained
  5. dry with materialwas dried over MgSO4
  6. concentrationconcentrated by rotary evaporation
  7. customThe residue was purified by flash column chromatography
  8. washeluting with 5% CH2Cl2/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-0ee23a9e93d6404f995cfad26ddfcd72
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785665B2

Notizen zur Reaktion

Wird geladen…