Water → samarium (R)-1,1'-bi-2-naphthol

HRID 1108534

Reaktionsgleichung

Reaktionsgleichung von HRID 1108534
[Cl-].[Cl-].[Cl-].[Sm+3:4].[Li].C([Li])CCC.[CH:11]1[CH:16]=[C:15]2[CH:17]=[CH:18][C:19]([OH:32])=[C:20]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][C:22]=3[OH:31])[C:14]2=[CH:13][CH:12]=1.CC(C)([O-])C.[Na+].O>C1COCC1.CCCCCC>[Sm:4].[CH:27]1[CH:26]=[C:25]2[CH:24]=[CH:23][C:22]([OH:31])=[C:21]([C:20]3[C:14]4[C:15](=[CH:16][CH:11]=[CH:12][CH:13]=4)[CH:17]=[CH:18][C:19]=3[OH:32])[C:30]2=[CH:29][CH:28]=1

Komponenten

9

Edukt 6

HCID 962WaterHCID 11762BinolHCID 3028194LithiumHCID 10131313Samarium(3+);trichlorideHCID 23676156Sodium t-butoxideHCID 178418339Butyllithium

Produkt 1

HCID 92015231samarium (R)-1,1'-bi-2-naphthol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel3×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a suspension of 128 mg (0.50 mmol) of anhydrous samarium trichloride (SmCl3) in 4.0 ml of THF were added, in an argon atmosphere at room temperature, a lithium binaphthoxide solution in THF [prepared by adding 1.25 ml (2.0 mmol) of a 1.6N n-butyllithium solution in hexane to a solution of 286.4 mg (1.0 mmol) of (R)-1,1'-bi-2-naphthol in 4.0 ml of THF], 48.1 mg (0.50 mmol) of sodium t-butoxide and 99 μl (5.5 mmol) of water, in that order, and the mixture was stirred at room temperature for 15 hours and then allowed to stand overnight to allow the insoluble matter to precipitate. The supernatant solution was submitted to the reaction proper as a samarium/(R)-1,1'-bi-2-naphthol complex solution (0.05 mmol/l).

Aufarbeitung

  1. additionwere added, in an argon atmosphere at room temperature
  2. waitto stand overnight
  3. customto precipitate
  4. customThe supernatant solution was submitted to the reaction proper as a samarium/(R)-1,1'-bi-2-naphthol complex solution (0.05 mmol/l)

Quellen und Nachweise

ORD-Eintrag
ord-13a51c2fd9064fb4ad338d07e58c5a99
Quelldatensatz
uspto-grants-2000_05
Patentnummer
USRE036718

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