Tetrabutylammonium Fluoride → HCID 21996979, compound

HRID 1637031Notes

Reaction equation

HRID 1637031 reaction equation
C([O:4][C:5]1[CH:19]=[CH:18][C:17]([C:20]#[C:21][Si](C)(C)C)=[CH:16][C:6]=1[C:7]([C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1)=[O:8])(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.O>[C:20]([C:17]1[CH:18]=[CH:19][C:5]([OH:4])=[C:6]([CH:16]=1)[C:7]([C:9]1[CH:10]=[CH:11][C:12]([CH3:15])=[CH:13][CH:14]=1)=[O:8])#[CH:21]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 21996961HCID 21996961, compound

Product 1

HCID 21996979HCID 21996979, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 100 mg (0.3 mmol) of 2-acetoxy-5-trimethylsilanylethynyl-4'-methylbenzophenone (Compound X) in 5 mL of tetrahydrofuran (under a blanket of argon) was added 0.86 mL (0.86 mmol) of tetrabutylammonium fluoride (1M in tetrahydrofuran). The resultant yellow solution was stirred at ambient temperature for 30 minutes, diluted with water (1 mL), extracted between ethyl ether and 10% HCl (aq.) solution, the layers separated and the aqueous phase washed with ethyl ether. The organic phases were combined, dried over MgSO4, filtered and concentrated in vacuo. Purification by flash chromatography (silica, 3% ethyl acetate in hexane) gave the title compound as an oil.

Workup

  1. extractionextracted between ethyl ether and 10% HCl (aq.) solution
  2. customthe layers separated
  3. washthe aqueous phase washed with ethyl ether
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (silica, 3% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-e886e87755f04c53b928034ad925d34a
Source dataset
uspto-grants-2000_03
Patent number
US06037488

Reaction notes

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