HCID 86724410, compound → HCID 86724417, compound

HRID 1778808Notes

Reaction equation

HRID 1778808 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.[CH:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][C:22]=1[C-:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32]1.[Li+]>CCOCC>[CH3:17][Si:7]([CH3:18])([CH:33]1[C:34]2[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:31]([C:22]2[CH:23]=[CH:24][C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:21]=2)=[CH:32]1)[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 86724418HCID 86724418, compound

Product 1

HCID 86724417HCID 86724417, 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-(2-naphthyl)indenide) (6.05 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 foam. The foam was extracted with pentane and the extracts were filtered to give a solution. The solution was evaporated under vacuum to give thick oil. Yield 9.44 g (98%). 1H NMR(C6D6): δ 8.20 (s, 1H), 7.84 (d, 1H), 7.76 (m, 2H), 7.70 (m, 2H) 7.51 (d, 1H), 7.27 (m, 4H), 6.71 (s, 1H), 3.75, (s, 1H), 2.94 (br s, 1H), 1.95 (s, 3H), 1.93 (s, 3H), 1.84 (s, 3H), 1.82 (s, 3H), −0.04 (s, 3H), −0.34 (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 foam
  6. extractionThe foam was extracted with pentane
  7. filtrationthe extracts were filtered
  8. customto give a solution
  9. customThe solution was evaporated under vacuum
  10. customto give thick oil

Sources & evidence

ORD record
ord-6149be1c2274416081cff9b64a9991eb
Source dataset
uspto-grants-2016_02
Patent number
US09266977B2

Reaction notes

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