Tetrabutylammonium Fluoride → HCID 17785853, compound

HRID 1422169Notes

Reaction equation

HRID 1422169 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:18]=[CH:17][C:10]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:8]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl>[C:6]([C:7]1[CH:18]=[CH:17][C:10]([O:11][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:9][CH:8]=1)#[CH:5]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 53781662HCID 53781662, compound

Product 1

HCID 17785853HCID 17785853, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl (4-trimethylsilylethynylphenoxy)acetate (20.00 g, 76 mmol) in dichloromethane (400 mL) was deaerated with argon. Tetrabutylammonium fluoride 24.40 g, 91 mmol) was added, and the mixture was stirred for 30 min at ambient temperature. The solution was washed with 10% aqueous citric acid (200 mL), water (5×400 mL), dried over Na2SO4 and concentrated. The residue was dissolved in diethyl ether and passed through a column filled with silica gel. Evaporation of diethyl ether yielded the title compound as a solid (12.63 g, 83%) which was chromatographically and spectroscopically identical with material synthesized previously (Takalo, H., Hemmila, I., Sutela, T. and Latva, M, 1996, Helv. Chim. Acta, 79, 789). Rf (A) 0.50.

Workup

  1. washThe solution was washed with 10% aqueous citric acid (200 mL), water (5×400 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolved in diethyl ether
  5. additionfilled with silica gel
  6. customEvaporation of diethyl ether

Sources & evidence

ORD record
ord-0a9db46cc90c4c70a8191ea43364dba9
Source dataset
uspto-grants-2000_06
Patent number
US06080839

Reaction notes

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