Tetrabutylammonium Fluoride → HCID 10242689, compound

HRID 1009908Notes

Reaction equation

HRID 1009908 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-2ed03e53bfdb490db7be3188a67f6f5c
Source dataset
uspto-grants-2011_07
Patent number
US07973163B2

Reaction notes

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