HCID 86724410, compound → HCID 86724409, compound

HRID 1778805Notes

Reaction equation

HRID 1778805 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.[C:21]([C:25]1[CH:30]=[CH:29][C:28]([C-:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]=[CH:32]2)=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22].[Li+]>CCOCC>[C:21]([C:25]1[CH:26]=[CH:27][C:28]([C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH:33]([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:32]=2)=[CH:29][CH:30]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 86724410HCID 86724410, compound2×HCID 86724411HCID 86724411, compound

Product 1

HCID 86724409HCID 86724409, 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-(4-t-butylphenyl)indenide) (6.20 g, 24.4 mmol, 1.07 eq.). The reaction was stirred for 18 hours, and was then evaporated under vacuum. The residue was extracted with pentane (40 mL) and the extract was filtered. The resulting solution was evaporated under vacuum to give a thick oil. Yield 10.11 g (104%). 1H NMR(C6D6): δ 7.83 (d, 1H), 7.67 (d, 2H), 7.50 (d, 1H), 7.41 (d, 2H), 7.26 (m, 2H), 6.64 (s, 1H), 3.71, (s, 1H), 2.95 (br s, 1H), 1.95 (s, 3H), 1.93 (s, 3H), 1.84 (s, 3H), 1.82 (s, 3H), 1.30 (s, 9H), −0.06 (s, 3H), −0.36 (s, 3H).

Workup

  1. customwas then evaporated under vacuum
  2. extractionThe residue was extracted with pentane (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-9b181cb2972845b3861a02fe46cf4e06
Source dataset
uspto-grants-2016_02
Patent number
US09266977B2

Reaction notes

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