Water → 2-Dipropylamino-8-trimethylstannyl-1,2,3,4-tetrahydronaphthalene

HRID 129930Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 129930
C([Li])CCC.Br[C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[CH2:15][CH:14]([N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])[CH2:13][CH2:12]2.[CH3:24][Sn:25](Cl)([CH3:27])[CH3:26].O>C1COCC1>[CH2:18]([N:17]([CH2:21][CH2:22][CH3:23])[CH:14]1[CH2:13][CH2:12][C:11]2[C:16](=[C:7]([Sn:25]([CH3:27])([CH3:26])[CH3:24])[CH:8]=[CH:9][CH:10]=2)[CH2:15]1)[CH2:19][CH3:20]

Komponenten

6

Edukt 4

HCID 962WaterHCID 14016Trimethyltin chlorideHCID 145295648-Bromo-2-dipropylamino-1,2,3,4-tetrahydronaphthaleneHCID 178418339Butyllithium

Produkt 1

HCID 194270892-Dipropylamino-8-trimethylstannyl-1,2,3,4-tetrahydronaphthaleneAusbeute 152,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Butyllithium (1.2M in hexane; 2.8 ml; 3.4 mmol) was added to a solution of 8-bromo-2-di-n-propylamino-1,2,3,4-tetrahydronaphthalene (1 g; 3.22 mmol) in THF (50 ml) at -78° C. After 1.5 hr., a solution of trimethyltin chloride (1.3 g, 2.0 mmol) in THF (20 ml) was added. The reaction mixture was allowed to warm to room temperature, stirred overnight at room temperature, poured into water, and extracted with methylene chloride. The extract was dried (Na2SO4) and concentrated to give the crude product. Purification by chromatography using 1:10 methanol:methylene chloride gave 1.2 g of the desired product which was used directly in the next step.

Aufarbeitung

  1. extractionextracted with methylene chloride
  2. dry with materialThe extract was dried (Na2SO4)
  3. concentrationconcentrated
  4. customto give the crude product
  5. customPurification by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-0f89195b860b4650ac558c089368650d
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05470977

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