Chlorodimethyl(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silane → HCID 131733074, compound

HRID 2179481Notes

Reaction equation

HRID 2179481 reaction equation
Cl[Si:2]([CH3:13])([CH3:12])[CH:3]1[C:7]([CH3:8])=[C:6]([CH3:9])[C:5]([CH3:10])=[C:4]1[CH3:11].[C:14]1([C-:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Li+]>CCOCC>[CH3:12][Si:2]([CH3:13])([CH:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:21]1)[CH:3]1[C:7]([CH3:8])=[C:6]([CH3:9])[C:5]([CH3:10])=[C:4]1[CH3:11]

Participants

4

Reactant 2

HCID 5045335Chlorodimethyl(2,3,4,5-tetramethyl-2,4-cyclopentadien-1-yl)silaneHCID 23707898HCID 23707898, compound

Product 1

HCID 131733074HCID 131733074, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of chlorodimethyl(2,3,4,5-tetramethylcyclopenta-2,4-dien-1-yl)silane (5.00 g, 23.3 mmol, 1.00 eq.) in ether (25 mL) at −35° C. was added lithium(1-phenylindenide) (4.85 g, 24.5 mmol, 1.05 eq.). The reaction was stirred for 23 hours, and the volatiles were then removed under vacuum. The residue was extracted with pentane (40 mL) and the extract was filtered. The resulting solution was evaporated under vacuum to give a thick oil. Yield 7.07 g (82%). 1H NMR (C6D6): δ 7.74 (d, 1H), 7.65 (d, 2H), 7.48 (d, 1H), 7.25 (m, 5H), 6.60 (s, 1H), 3.69, (s, 1H), 2.92 (br s, 1H), 1.93 (s, 3H), 1.90 (s, 3H), 1.82 (s, 3H), 1.821 (s, 3H), −0.09 (s, 3H), −0.39 (s, 3H).

Workup

  1. customthe volatiles were then removed under vacuum
  2. extractionThe residue was extracted with pentane (40 mL)
  3. filtrationthe extract was filtered
  4. customThe resulting solution was evaporated under vacuum
  5. customto give a thick oil

Sources & evidence

ORD record
ord-f2d316e1035241d9a9f1244ae3bada17
Source dataset
uspto-grants-2015_06
Patent number
US09068033B2

Reaction notes

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