2,6-Lutidine → tert-Butyldimethylsilyloxy-1-phenyl-prop-1-yne

HRID 2059

Reaktionsgleichung

Reaktionsgleichung von HRID 2059
[C:1]1([CH:7](O)[C:8]#[CH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C(C)=CC=CC=1C.FC(F)(F)S([O:24][Si:25]([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26])(=O)=O>ClCCl>[Si:25]([O:24][CH2:9][C:8]#[C:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Komponenten

5

Edukt 3

HCID 79372,6-LutidineHCID 20155alpha-EthynylbenzenemethanolHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonate

Produkt 1

HCID 10610466tert-Butyldimethylsilyloxy-1-phenyl-prop-1-yne

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-Phenyl-2-propyn-1-ol (7 g) was dissolved in dichloromethane at 0° C. under nitrogen. 2,6-Lutidine (6.17 ml) was added to the solution followed by dropwise addition of tert-butyldimethylsilyl trifluoromethane sulfonate (12.16 ml); the resulting solution was stirred overnight at room temperature. The dichloromethane was washed with water (2×), brine and dried (MgSO4) and solvent removed in vacuo. The residue was purified on flash silica using 100% petrol moving to 5% ethyl acetate/petrol, to afford the title compound as a yellow oil (10.31 g).

Aufarbeitung

  1. washThe dichloromethane was washed with water (2×), brine
  2. dry with materialdried (MgSO4) and solvent
  3. customremoved in vacuo
  4. customThe residue was purified on flash silica using 100% petrol moving to 5% ethyl acetate/petrol

Quellen und Nachweise

ORD-Eintrag
ord-df8b8caa74ee4e36b45ccc97b1be26b5
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728695

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