Pyridine → 4-(Triethylsilyl)but-3-yn-1-yl 4-methylbenzene-1-sulfonate

HRID 58639

Reaktionsgleichung

Reaktionsgleichung von HRID 58639
[CH2:1]([Si:3]([CH2:11][CH3:12])([CH2:9][CH3:10])[C:4]#[C:5][CH2:6][CH2:7][OH:8])[CH3:2].[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.N1C=CC=CC=1>ClCCl>[CH3:23][C:13]1[CH:18]=[CH:17][C:16]([S:19]([O:8][CH2:7][CH2:6][C:5]#[C:4][Si:3]([CH2:1][CH3:2])([CH2:9][CH3:10])[CH2:11][CH3:12])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 27606944-(Triethylsilyl)-3-butyn-1-ol

Produkt 1

HCID 120301384-(Triethylsilyl)but-3-yn-1-yl 4-methylbenzene-1-sulfonateAusbeute 102,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-(triethylsilyl)but-3-yn-1-ol (2 mL; 9.22 mmol), p-toluensulfonyl chloride (3.52 g; 18.44 mmol) and pyridine (1.49 mL; 18.44 mmol) in dichloromethane (30 mL) was stirred at room temperature for 3 days. The reaction mixture was then washed with a saturated solution of sodium hydrogen sulphate and brine. The organic layer was dried, concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane) to yield 3.20 g (quantitative yield) of 4-(triethylsilyl)but-3-ynyl 4-methylbenzenesulfonate as a yellow oil.

Aufarbeitung

  1. washThe reaction mixture was then washed with a saturated solution of sodium hydrogen sulphate and brine
  2. customThe organic layer was dried
  3. concentrationconcentrated under reduced pressure
  4. customthe crude material was purified by flash chromatography on silica gel (eluent 2 to 20% ethyl acetate in heptane)

Quellen und Nachweise

ORD-Eintrag
ord-d234e0a59861469e8cf4dcbff74c6ff4
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434722B2

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