Triethylamine → (But-3-yn-1-yloxy)(tert-butyl)dimethylsilane

HRID 73307

Reaktionsgleichung

Reaktionsgleichung von HRID 73307
[CH:1]#[C:2][CH2:3][CH2:4][OH:5].[Si:6](Cl)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].C(N(CC)CC)C>ClCCl>[C:9]([Si:6]([O:5][CH2:4][CH2:3][C:2]#[CH:1])([CH3:8])[CH3:7])([CH3:12])([CH3:11])[CH3:10]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 135663-Butyn-1-OLHCID 28928tert-Butyldimethylsilyl chloride

Produkt 1

HCID 4304567(But-3-yn-1-yloxy)(tert-butyl)dimethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stirred, 0° C. solution of homopropargyl alcohol (10 g, 0.14 mol) and tert-butyldimethylsilyl chloride (21.5 g, 0.14 mol) in dichloromethane (50 mL) was treated with triethylamine (22.8 mL, 0.168 mol). The mixture was then stirred overnight at room temperature. The mixture was washed with water and the organic layer was dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by chromatography (95:5 hexane/ethyl acetate) to provide the title compound. 1H NMR (300 MHz, CDCl3): δ 0.08 (s, 6H), 0.90 (s, 9H), 1.96 (t, J=3 Hz, 1H), 2.41 (dt, J=6 Hz, J=3 Hz, 2H), 3.75 (d, J=6 Hz, 2H).

Aufarbeitung

  1. washThe mixture was washed with water
  2. dry with materialthe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by chromatography (95:5 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-6062a4876b694fceb2ae19de7916a7cc
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829041B2

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