HCID 86724410, compound → HCID 86724420, compound

HRID 1778809Notes

Reaction equation

HRID 1778809 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:30]=[CH:29][C:28]([CH3:31])=[C:27]2[C:23]=1[CH:24]=[CH:25][C-:26]2[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[Li+]>CCOCC>[CH3:31][C:28]1[CH:29]=[CH:30][C:22]([CH3:21])=[C:23]2[C:27]=1[C:26]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[CH:25][CH:24]2[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]

Participants

4

Reactant 2

HCID 86724410HCID 86724410, compound2×HCID 86724421HCID 86724421, compound

Product 1

HCID 86724420HCID 86724420, 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 (4,7-dimethyl-1-phenylindenide) (5.53 g, 24.4 mmol, 1.07 eq.). The reaction was stirred for 25 hours, and was then evaporated under vacuum. The residue was extracted with pentane (3×40 mL) and the extract was filtered. The resulting solution was evaporated under vacuum to give a thick oil. Yield 9.07 g (100%). 1H NMR(C6D6): δ 7.41 (d, 2H), 7.19 (m, 2H), 6.97 (s, 3H), 6.45 (d, 1H), 3.78, (s, 1H), 2.86 (br s, 1H), 2.30 (s, 3H), 2.13 (s, 3H), 1.96 (s, 3H), 1.89 (s, 3H), 1.78 (s, 3H), 1.77 (s, 3H), −0.04 (s, 3H), −0.32 (s, 3H).

Workup

  1. customwas then evaporated under vacuum
  2. extractionThe residue was extracted with pentane (3×40 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-0cda8505cc5442cb8d2077f7ec64caba
Source dataset
uspto-grants-2016_02
Patent number
US09266977B2

Reaction notes

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