Tetrabutylammonium Fluoride → HCID 21996979, compound

HRID 1976328Notes

Reaction equation

HRID 1976328 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-trimethylsilanylethynyl4′-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-9dc0000549b24c6394634dcbcc0ab4c3
Source dataset
uspto-grants-2001_05
Patent number
US06225494B1

Reaction notes

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