Triethylamine → 1-((2R,5R)-2,5-Dimethylpyrrolidinyl)-2-diphenylphosphinonaphthalene

HRID 1292639Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1292639
[CH3:1][C@@H:2]1[CH2:6][CH2:5][C@@H:4]([CH3:7])[N:3]1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[P:18]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O.C(N(CC)CC)C.Cl[SiH](Cl)Cl.[OH-].[Na+]>C1(C)C(C)=CC=CC=1>[CH3:1][C@@H:2]1[CH2:6][CH2:5][C@@H:4]([CH3:7])[N:3]1[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[P:18]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 24811TrichlorosilaneHCID 541313931-((2R,5R)-2,5-dimethylpyrrolidinyl)-2-diphenylphosphinylnaphthalene

Produkt 1

HCID 539401591-((2R,5R)-2,5-Dimethylpyrrolidinyl)-2-diphenylphosphinonaphthaleneAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7237O-XyleneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

To a solution of 3.3 g (7.8 mmol) of the 1-((2R,5R)-2,5-dimethylpyrrolidinyl)-2-diphenylphosphinylnaphthalene in 100 ml of xylene were added 6.8 ml (49.14 mmol) of triethylamine and 4.7 ml (46.8 mmol) of trichlorosilane, and the mixture was slowly heated up to 120° C., at which the mixture was stirred for 6.5 hours. After cooling to room temperature, the reaction mixture was poured into 250 ml of 2N NaOH and extracted with benzene. The extract was washed with water and dried over anhydrous magnesium sulfate. The crude product was purified by silica gel column chromatography (hexane/acetone=20/1 by volume) to give 2.71 g of the title compound in a yield of 85%.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with benzene
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe crude product was purified by silica gel column chromatography (hexane/acetone=20/1 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-40635a258097496db5e72971eb2c9698
Quelldatensatz
uspto-grants-1998_05
Patentnummer
US05756760

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