Triethylamine → 6-((di-tert-Butylphosphino)methyl)-2,2'-bipyridine

HRID 2167163

Reaktionsgleichung

Reaktionsgleichung von HRID 2167163
Cl[CH2:2][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=[CH:5][CH:4]=1.[C:15]([PH:19][C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>CO>[C:15]([P:19]([CH2:2][C:3]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[CH:6]=[CH:5][CH:4]=1)[C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])([CH3:17])[CH3:16]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 136643Phosphine, bis(1,1-dimethylethyl)-HCID 6428432,2'-Bipyridine, 6-(chloromethyl)-

Produkt 1

HCID 532341466-((di-tert-Butylphosphino)methyl)-2,2'-bipyridineAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To an oven dried 50 mL pressure vessel equipped with magnetic stirring bar was added 6-chloromethyl-2,2′-bipyridine (BPy-CH2Cl) (2.05 g, 10.00 mmol), di-tert-butyl phosphine (1.75 g, 12.00 mmol), and 30 mL MeOH in a nitrogen glove box. The flask was sealed and heated at 50° C. for 48 hrs with stirring outside the glove box. After cooling, it was reintroduced to the glove box, triethylamine (1.82 g, 18.00 mmol) was added and the reaction mixture was stirred at room temperature for 1 hr. The solvents were removed under reduced pressure to obtain a white solid. The residue was washed with ether (3×20 mL) and the ether filtered and was removed under reduced pressure to yield a white solid. It was recrystallized from MeOH at ca. −30° C. to yield 2.67 g (85%) of 6-di-tert-butylphosphinomethyl-2,2′-bipyridine (BPy-tPNN).

Aufarbeitung

  1. customTo an oven dried 50 mL pressure vessel
  2. customequipped with magnetic stirring bar
  3. customThe flask was sealed
  4. temperatureAfter cooling
  5. additionwas added
  6. stirringthe reaction mixture was stirred at room temperature for 1 hr
  7. customThe solvents were removed under reduced pressure
  8. customto obtain a white solid
  9. washThe residue was washed with ether (3×20 mL)
  10. filtrationthe ether filtered
  11. customwas removed under reduced pressure
  12. customto yield a white solid
  13. customIt was recrystallized from MeOH at ca. −30° C.

Quellen und Nachweise

ORD-Eintrag
ord-b309024d2e2b451fbcb6027f7fc5c0a6
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045381B2

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