HCID 86724410, compound → HCID 86724415, compound

HRID 1778807Notes

Reaction equation

HRID 1778807 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]([C-:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]=[CH:30]2)[CH:25]=[C:26]([CH3:28])[CH:27]=1.[Li+]>CCOCC>[CH3:28][C:26]1[CH:25]=[C:24]([C:29]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH:31]([Si:7]([CH3:17])([CH3:18])[CH:8]3[C:12]([CH3:13])=[C:11]([CH3:14])[C:10]([CH3:15])=[C:9]3[CH3:16])[CH:30]=2)[CH:23]=[C:22]([CH3:21])[CH:27]=1

Participants

4

Reactant 2

HCID 86724410HCID 86724410, compound2×HCID 86724416HCID 86724416, compound

Product 1

HCID 86724415HCID 86724415, 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 (1-(3,5-dimethylphenyl)indenide) (5.53 g, 24.4 mmol, 1.07 eq.). The reaction was stirred for 19 hours, and was then evaporated under vacuum. The residue was extracted with pentane (40 mL, then 2×20 mL) and the extract was filtered. The resulting solution was evaporated under vacuum to give a sticky solid. Yield 9.65 g (106%). 1H NMR(C6D6): δ 7.87 (d, 1H), 7.40 (s, 2H), 7.25 (m, 2H), 6.88 (s, 1H), 6.64 (s, 1H), 3.73, (s, 1H), 2.93 (br s, 1H), 2.23 (s, 6H), 1.93 (s, 3H), 1.92 (s, 3H), 1.84 (s, 3H), 1.82 (s, 3H), −0.07 (s, 3H), −0.36 (s, 3H).

Workup

  1. customwas then evaporated under vacuum
  2. extractionThe residue was extracted with pentane (40 mL
  3. filtration2×20 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-1a6cb5c1224440a1842ab4fbe315d805
Source dataset
uspto-grants-2016_02
Patent number
US09266977B2

Reaction notes

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