HCID 22023067, compound → HCID 131734810, compound

HRID 1778455Notes

Reaction equation

HRID 1778455 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.[CH2:21]([C:23]1[CH-:24][C:25]2[C:30]([CH:31]=1)=[C:29]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH:28]=[CH:27][CH:26]=2)[CH3:22].[Li+]>CCOCC>[CH3:17][Si:7]([CH3:18])([CH:24]1[C:25]2[C:30](=[C:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:28]=[CH:27][CH:26]=2)[CH:31]=[C:23]1[CH2:21][CH3:22])[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 22023067HCID 22023067, compoundHCID 86724410HCID 86724410, compound

Product 1

HCID 131734810HCID 131734810, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a green solution of dimethyl(2,3,4,5-tetramethylcyclopenta-2,4-dien-1-yl)silyl trifluoromethanesulfonate (7.50 g, 22.8 mmol, 1.00 eq.) in ether (25 mL) at −35° C. was added lithium (2-ethyl-4-phenylindenide) (5.53 g, 24.4 mmol, 1.07 equiv.) in portions to give a hazy yellow solution near room temperature. The reaction was stirred for 20 hours, then evaporated under vacuum, leaving a light yellow semi-solid. The residue was extracted with pentane (3×40 mL) and the extract was filtered to give a yellow solution and pale yellow-white solid. The solution was evaporated under vacuum to yield thick, yellow oil. Yield 9.28 g (102%). 1H NMR(C6D6): δ 7.64 (d, 2H), 7.43 (d, 1H), 7.35 (d, 1H), 7.29 (t, 2H), 7.19 (t, 2H), 6.95 (s, 1H), 3.74, (s, 1H), 3.17 (br s, 1H), 2.46 (m, 1H), 2.32 (m, 1H), 1.95 (s, 3H), 1.89 (s, 3H), 1.82 (s, 6H), 1.05 (t, 3H), −0.22 (s, 6H).

Workup

  1. customto give a hazy yellow solution near room temperature
  2. customevaporated under vacuum
  3. customleaving a light yellow semi-solid
  4. extractionThe residue was extracted with pentane (3×40 mL)
  5. filtrationthe extract was filtered
  6. customto give a yellow solution and pale yellow-white solid
  7. customThe solution was evaporated under vacuum
  8. customto yield thick

Sources & evidence

ORD record
ord-91de6a9887ef43a081261629981047b1
Source dataset
uspto-grants-2016_02
Patent number
US09266910B2

Reaction notes

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