Tetrabutylammonium Fluoride → HCID 10242689, compound

HRID 735732Notes

Reaction equation

HRID 735732 reaction equation
[Si]([O:8][CH2:9][CH2:10][N:11]([CH3:23])[C:12]1[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[OH:8][CH2:9][CH2:10][N:11]([CH3:23])[C:12]1[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57847252HCID 57847252, compound

Product 1

HCID 10242689HCID 10242689, compoundYield 72.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (30 ml) of ethyl 4-[(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl) (methyl)amino]benzoate (2.33 g, 6.90 mmol) in tetrahydrofuran was added tetrabutyl ammoniumfluoride (1.0 M toluene solution, 10.4 ml, 10.4 mmol) at room temperature and the mixture was stirred overnight. After concentration of the reaction mixture under reduced pressure, the residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (3:2-1:4, v/v) to give the title compound (1.11 g, 72%) as a colorless oil.

Workup

  1. washeluted with hexane-ethyl acetate (3:2-1:4, v/v)

Sources & evidence

ORD record
ord-6057ab1faf9a4c1595d6d4dacdaaf9ca
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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