Tributyltin Chloride → 4-Cyclopentyloxy-2-tributylstannanyl-pyridine

HRID 1898597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1898597
Br[C:2]1[CH:7]=[C:6]([O:8][CH:9]2[CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=1.[Cl-].[Li+].C([Mg]Cl)(C)C.[CH2:21]([Sn:25](Cl)([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:26][CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH3:24]>C1COCC1>[CH:9]1([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Sn:25]([CH2:26][CH2:27][CH2:28][CH3:29])([CH2:30][CH2:31][CH2:32][CH3:33])[CH2:21][CH2:22][CH2:23][CH3:24])[CH:7]=2)[CH2:13][CH2:12][CH2:11][CH2:10]1

Komponenten

5

Edukt 3

HCID 15096Tributyltin ChlorideHCID 457879742-Bromo-4-cyclopentyloxy-pyridineHCID 178461733HCID 178461733, Verbindung2×

Produkt 1

HCID 575166364-Cyclopentyloxy-2-tributylstannanyl-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

In a round bottomed flask 2-bromo-4-cyclopentyloxy-pyridine (339 mg, 1.40 mmol) was dissolved in THF (6 mL). The solution was cooled to 0° C. and isopropylmagnesium chloride lithium chloride complex (1.3 M in THF, 1.1 mL, 1.47 mmol) was added dropwise. The reaction mixture was stirred at 0° C. for 15 min then at room temperature for 2 h. An additional portion of isopropylmagnesium chloride lithium chloride complex (1.3 M in THF, 0.27 mL, 0.35 mmol) was added and stirring was continued at room temperature for 30 min. Tributyltin chloride (0.42 mL, 1.54 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4 and concentrated to give 4-cyclopentyloxy-2-tributylstannanyl-pyridine as a light brown oil which was used without further purification.

Aufarbeitung

  1. waitat room temperature for 2 h
  2. stirringstirring
  3. waitwas continued at room temperature for 30 min
  4. stirringthe reaction mixture was stirred at room temperature for 2 h
  5. customThe reaction mixture was quenched with water
  6. extractionextracted with ethyl acetate
  7. washThe organic phase was washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2b9fbe9f3d284f7987d42199a1f30ed5
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518945B2

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