Triethylamine → [(e)-5-(4-Bromo-2-thienyl)-1,1-diethylhept-4-enyloxy]triethylsilane

HRID 49344

Reaktionsgleichung

Reaktionsgleichung von HRID 49344
[Br:1][C:2]1[CH:3]=[C:4](/[C:7](/[CH2:17][CH3:18])=[CH:8]/[CH2:9][CH2:10][C:11]([CH2:15][CH3:16])([OH:14])[CH2:12][CH3:13])[S:5][CH:6]=1.CN(C1C=CC=CN=1)C.C(N(CC)CC)C.FC(F)(F)S(O[Si:41]([CH2:46][CH3:47])([CH2:44][CH3:45])[CH2:42][CH3:43])(=O)=O>ClCCl.O>[Br:1][C:2]1[CH:3]=[C:4](/[C:7](/[CH2:17][CH3:18])=[CH:8]/[CH2:9][CH2:10][C:11]([CH2:15][CH3:16])([CH2:12][CH3:13])[O:14][Si:41]([CH2:46][CH3:47])([CH2:44][CH3:45])[CH2:42][CH3:43])[S:5][CH:6]=1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 69824523(e)-7-(4-Bromo-2-thienyl)-3-ethylnon-6-en-3-ol

Produkt 1

HCID 69825241[(e)-5-(4-Bromo-2-thienyl)-1,1-diethylhept-4-enyloxy]triethylsilane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

11.8 g (35.6 mmol) of (E)-7-(4-bromo-2-thienyl)-3-ethylnon-6-en-3-ol are dissolved in 150 mL of dichloromethane. 130 mg (1.1 mmol) of dimethylaminopyridine and 14.9 mL (107 mmol) of triethylamine are added. The reaction medium is cooled to 0° C. and 12.1 mL (53.4 mmol) of triethylsilyl trifluoromethanesulphonate are added dropwise. The medium is warmed to room temperature and stirred for 15 minutes, after which it is poured into 150 mL of water and extracted with dichloromethane. After chromatography on silica gel (eluent: heptane), the desired product is obtained in the form of a colourless oil (m=15 g; Y=100%).

Aufarbeitung

  1. temperatureThe medium is warmed to room temperature
  2. extractionextracted with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-61c3221b133044d69ab1c621e42a83c4
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706725B1

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