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

HRID 2208629Notes

Reaction equation

HRID 2208629 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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 (C6D6): δ 7.59 (d, 2H), 7.44 (m, IH), 7.36 (m, 3H), 7.22 (m, 2H), 6.86 (d, 1H), 3.42 (d, IH), 2.11 (d, 3H), 0.27 (s, 3H), −0.03 (s, 3H).

Workup

  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

Sources & evidence

ORD record
ord-91f3c20b9bb04217a1491508f43b3c1a
Source dataset
uspto-grants-2016_06
Patent number
US09376559B2

Reaction notes

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