Chlorotrimethylsilane → HCID 18357295, Verbindung

HRID 428345Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 428345
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Li].C[Si](Cl)(C)C.[CH:15]([N:18]([CH:28]([CH3:30])[CH3:29])[C:19](=[O:27])[CH:20]=[CH:21][C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)([CH3:17])[CH3:16]>CSC.C(OCC)C>[CH:28]([N:18]([CH:15]([CH3:17])[CH3:16])[C:19](=[O:27])[CH2:20][CH:21]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)([CH3:30])[CH3:29]

Komponenten

6

Edukt 3

HCID 6397ChlorotrimethylsilaneHCID 4444087N,N-Diisopropyl-3-(2-thienyl)propenamideHCID 178506687HCID 178506687, Verbindung

Produkt 1

HCID 18357295HCID 18357295, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1068Dimethyl SulfideLösungsmittelHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

Copper(I)bromide dimethyl sulfide complex (4.63 g 22.5 mmol) was dissolved in dimethyl sulfide (18 mL), and diethyl ether (15 mL). The solution was cooled to 0° C., whereafter 2-methoxyphenyllithium (41.2) (45 mmol) was added. After 10 min., the temperature was lowered to −78° C. Trimethylsilylchloride (4.89 g, 45.0 mmol) was added, followed by N,N-diisopropyl-3-(2-thienyl)propenamide (41.1) (3.56 g, 15 mmol) in diethyl ether (20 mL). The temperature was allowed to slowly rise to room temperature overnight. The reaction was quenched with saturated NH4Cl (10 mL) and conc. ammonia (10 mL). Diethyl ether (80 mL) was added and the mixture was filtered through Celite. The aqueous phase was extracted twice with diethyl ether. The combined organic phases were washed once with brine and dried (MgSO4). The solvent was evaporated and the crude product was chromatographed on silica (petroleum ether-ethyl acetate 3:1), affording a yellow oil, 3.75 g (73%): 1H NMR (CDCl3) d 1.12 (t, 6H), 1.29 (t, 6H), 3.02 (m, 2H), 3.4 (br, 1H), 3.80 (s, 3H), 4.03 (m, 1H), 5.26 (t, 1H), 6.8-7.3 (m, 7H).

Aufarbeitung

  1. additionwas added
  2. customwas lowered to −78° C
  3. waitto slowly rise to room temperature overnight
  4. customThe reaction was quenched with saturated NH4Cl (10 mL) and conc. ammonia (10 mL)
  5. additionDiethyl ether (80 mL) was added
  6. filtrationthe mixture was filtered through Celite
  7. extractionThe aqueous phase was extracted twice with diethyl ether
  8. washThe combined organic phases were washed once with brine
  9. dry with materialdried (MgSO4)
  10. customThe solvent was evaporated
  11. customthe crude product was chromatographed on silica (petroleum ether-ethyl acetate 3:1)
  12. customaffording a yellow oil, 3.75 g (73%)

Quellen und Nachweise

ORD-Eintrag
ord-7d8c3fcafa8c48e68ccc416205efb9e8
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313132B1

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