HCID 86724410, compound → HCID 86724423, compound

HRID 1778810Notes

Reaction equation

HRID 1778810 reaction equation
FC(F)(F)S(O[Si:7]([CH3:18])([CH3:17])[CH:8]1[C:12]([CH3:13])=[C:11]([CH3:14])[C:10]([CH3:15])=[C:9]1[CH3:16])(=O)=O.[CH3:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][C:30]=1[CH3:31])[C-:27]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:26]=[CH:25]2.[Li+]>CCOCC>[CH3:31][C:30]1[CH:29]=[C:28]2[C:24](=[CH:23][C:22]=1[CH3:21])[CH:25]([Si:7]([CH3:17])([CH3:18])[CH:8]1[C:12]([CH3:13])=[C:11]([CH3:14])[C:10]([CH3:15])=[C:9]1[CH3:16])[CH:26]=[C:27]2[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 86724410HCID 86724410, compound2×HCID 86724424HCID 86724424, compound

Product 1

HCID 86724423HCID 86724423, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of dimethyl(2,3,4,5-tetramethylcyclopenta-2,4-dien-1-yl)silyl trifluoromethanesulfonate (Compound C, 7.50 g, 22.8 mmol, 1.00 eq.) in ether (25 mL) at −35° C. was added lithium (5,6-dimethyl-1-phenylindenide) (5.53 g, 24.4 mmol, 1.07 eq.). The reaction was stirred for 24 hours, and was then evaporated under vacuum. The residue was extracted with pentane (40 mL, then 2×25 mL) and the extract was filtered. The resulting solution was evaporated under vacuum to give a sticky solid. Yield 9.34 g (103%). 1H NMR(C6D6): δ 7.71 (d, 2H), 7.62 (s, 1H), 7.36 (s, 1H), 7.31 (t, 2H), 7.20 (m, 1H), 6.57 (s, 1H), 3.70, (s, 1H), 2.98 (br s, 1H), 2.23 (s, 3H), 2.17 (s, 3H), 1.97 (s, 3H), 1.95 (s, 3H), 1.84 (s, 6H), −0.04 (s, 3H), −0.32 (s, 3H).

Workup

  1. customwas then evaporated under vacuum
  2. extractionThe residue was extracted with pentane (40 mL
  3. filtration2×25 mL) and the extract was filtered
  4. customThe resulting solution was evaporated under vacuum
  5. customto give a sticky solid

Sources & evidence

ORD record
ord-f4bfd9e370164834a78a6f285a77b5e9
Source dataset
uspto-grants-2016_02
Patent number
US09266977B2

Reaction notes

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