Dichlorodimethylsilane → Dimethyl(2-methyl-4-phenylindenyl)silyl chloride

HRID 1778453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1778453
Cl[Si:2]([Cl:5])([CH3:4])[CH3:3].[CH3:6][C:7]1[CH-:8][C:9]2[C:14]([CH:15]=1)=[C:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:12]=[CH:11][CH:10]=2.[Li+]>CCOCC>[Cl:5][Si:2]([CH3:3])([CH3:4])[CH:8]1[C:9]2[C:14](=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:12]=[CH:11][CH:10]=2)[CH:15]=[C:7]1[CH3:6]

Komponenten

4

Edukt 2

HCID 6398DichlorodimethylsilaneHCID 22023019Lithium 2-methyl-4-phenylindenide

Produkt 1

HCID 21943894Dimethyl(2-methyl-4-phenylindenyl)silyl chloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To a colorless solution of dichlorodimethylsilane (12.90 g, 100 mmol, 3.00 eq.) in ether (30 ml) at −30° C. was added lithium (2-methyl-4-phenylindenide) (7.07 g, 33.3 mmol, 1.00 equiv.) in portions to give a cloudy yellow mixture. The reaction was allowed to warm to room temperature and stirred for 4 hours, becoming cloudy white with precipitate. The mixture was evaporated under vacuum, leaving a white solid. The solid was extracted with pentane (40 ml), and the extract was filtered to give a light yellow solution and white solid. The solution was evaporated under vacuum, leaving a white solid. Yield 9.85 g (99%). 1H NMR(C6 D6): δ7.59 (d, 2H), 7.44 (m, 1H), 7.36 (m, 3H), 7.22 (m, 2H), 6.86 (d, 1H), 3.42 (d, 1H), 2.11 (d, 3H), 0.27 (s, 3H), −0.03 (s, 3H).

Aufarbeitung

  1. customto give a cloudy yellow mixture
  2. customThe mixture was evaporated under vacuum
  3. customleaving a white solid
  4. extractionThe solid was extracted with pentane (40 ml)
  5. filtrationthe extract was filtered
  6. customto give a light yellow solution and white solid
  7. customThe solution was evaporated under vacuum
  8. customleaving a white solid

Quellen und Nachweise

ORD-Eintrag
ord-95582c9d95d54b5f8cf1d79ae44e2abc
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266910B2

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