Tetrabutylammonium Fluoride → HCID 18334185, compound

HRID 2269430Notes

Reaction equation

HRID 2269430 reaction equation
[Si]([O:8][CH:9]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:10][NH:11][CH:12]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)(=O)C>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([CH:12]([NH:11][CH2:10][CH:9]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[OH:8])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18334230HCID 18334230, compound

Product 1

HCID 18334185HCID 18334185, compoundYield 85.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-[2-(t-butyl-dimethylsilyloxy)-2-phenylethyl]-N-[(4-methoxyphenyl)-(3-nitrophenyl)methyl]amine (4.95 g) [prepared as described in step (a) above] and a solution of tetrabutylammonium fluoride in tetrahydrofuran (1M, 20 ml) was stirred at ambient temperature for 1 hour. The reaction mixture was diluted with ethyl acetate, and the ethyl acetate was washed with water and with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then evaporated under reduced pressure. The residue was purified by chromatography through a silica gel column using a 3:1 by volume mixture of cyclohexane and ethyl acetate as the eluant, to afford the title compound (3.26 g) as a pale yellow oil.

Workup

  1. washthe ethyl acetate was washed with water and with an aqueous solution of sodium chloride
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue was purified by chromatography through a silica gel column
  5. additionby volume mixture of cyclohexane and ethyl acetate as the eluant

Sources & evidence

ORD record
ord-398b034bca3e4363ae3fc73859727a29
Source dataset
uspto-grants-2001_12
Patent number
US06329405B1

Reaction notes

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