Tetrabutylammonium Fluoride → HCID 69087933, compound

HRID 990616Notes

Reaction equation

HRID 990616 reaction equation
[O:1]([C:9]1[CH:10]=[C:11]([CH2:15][O:16][CH:17]=[C:18]2[CH2:25][CH2:24][CH:23]3[CH2:26][CH:19]2[CH:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:21]=[C:22]3[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:12]=[CH:13][CH:14]=1)[Si](C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:1][C:9]1[CH:10]=[C:11]([CH2:15][O:16][CH:17]=[C:18]2[CH2:25][CH2:24][CH:23]3[CH2:26][CH:19]2[CH:20]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:21]=[C:22]3[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131723537HCID 131723537, compound

Product 1

HCID 69087933HCID 69087933, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 9.6 parts of (3-tert-Butyldimethylsiloxyphenyl) methoxy methylene-2,4-diphenyl bicyclo(3.3.1]non-2-ene (78) in 100 mL of THF was added 9 parts of 70% tetra-n-butylammonium fluoride in 30 mL of THF over a period of 10 minutes and stirring was continued for two hours. TLC on silica gel plate showed the formation of new product. Solvent was evaporated under reduced pressure and the oily material was dissolved in 300 mL of methylene chloride and washed with 2×100 mL of water. After drying over anhydrous sodium sulfate, the solvent was evaporated and the oily product was purified on silica gel column. TLC on silica gel plate of the fractions were checked and the combined organic solvent was evaporated, yield 6.24 parts. The structure of the product was confirmed on the basis of 1H NMR. The reaction proceeded as follows:

Workup

  1. customSolvent was evaporated under reduced pressure
  2. dissolutionthe oily material was dissolved in 300 mL of methylene chloride
  3. washwashed with 2×100 mL of water
  4. dry with materialAfter drying over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customthe oily product was purified on silica gel column
  7. customthe combined organic solvent was evaporated
  8. customyield 6.24 parts

Sources & evidence

ORD record
ord-81978dc6af1c404790ff189974706659
Source dataset
uspto-grants-2002_10
Patent number
US06461876B1

Reaction notes

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