Tetramethylcyclopentadienylsodium → dimethyl (2-methyl-4-phenyl-1H-indenyl)(2,3,4,5-tetramethylcyclopenta-dienyl)silane

HRID 2208630Notes

Reaction equation

HRID 2208630 reaction equation
Cl[Si:2]([CH3:20])([CH3:19])[CH:3]1[C:11]2[C:6](=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[CH3:18].[CH3:21][C:22]1[CH-:26][C:25]([CH3:27])=[C:24]([CH3:28])[C:23]=1[CH3:29].[Na+]>O1CCCC1>[CH3:19][Si:2]([CH3:20])([CH:3]1[C:11]2[C:6](=[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]1[CH3:18])[C:26]1[CH:25]([CH3:27])[C:24]([CH3:28])=[C:23]([CH3:29])[C:22]=1[CH3:21]

Participants

4

Reactant 2

HCID 15823254TetramethylcyclopentadienylsodiumHCID 21943894Dimethyl(2-methyl-4-phenylindenyl)silyl chloride

Product 1

HCID 131735970dimethyl (2-methyl-4-phenyl-1H-indenyl)(2,3,4,5-tetramethylcyclopenta-dienyl)silane

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a light yellow solution of chlorodimethyl(2-methyl-4-phenyl-1H-indenyl)silane (9.40 g, 31.4 mmol, 1.00 eq.) in tetrahydrofuran (40 mL) at −30° C. was added sodium (tetramethylcyclopentadienide) (4.76 g, 33.0 mmol, 1.05 equiv.) in portions to give a cloudy orange solution. The reaction was allowed to warm to room temperature and stirred for 23 hours. The mixture was evaporated under vacuum leaving an orange residue. The residue was extracted with pentane (50 mL) and the extract was filtered to give a bright yellow solution and yellow solid. The solution was evaporated under vacuum to yield thick, orange oil. Yield 10.16 g (84%). 1H NMR (C6D6): δ 7.61 (d, 2H), 7.41 (m, IH), 7.31 (m, 4H), 7.19 (m, IH), 6.85 (s, IH), 3.60, (s, IH), 3.16 (br s, IH), 2.00 (s, 3H), 1.93 (s, 3H), 1.88 (s, 3H), 1.82 (s, 6H), −0.23 (s, 3H), −0.24 (s, 3H).

Workup

  1. customto give a cloudy orange solution
  2. customThe mixture was evaporated under vacuum
  3. customleaving an orange residue
  4. extractionThe residue was extracted with pentane (50 mL)
  5. filtrationthe extract was filtered
  6. customto give a bright yellow solution and yellow solid
  7. customThe solution was evaporated under vacuum
  8. customto yield thick

Sources & evidence

ORD record
ord-152717cb27e44c43af3828aa015bf880
Source dataset
uspto-grants-2016_06
Patent number
US09376559B2

Reaction notes

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