Tetrabutylammonium Fluoride → Methyl 2-(4-hydroxymethylphenoxy)-3-phenylpropanoate

HRID 2399502Notes

Reaction equation

HRID 2399502 reaction equation
[Si]([O:8][CH2:9][C:10]1[CH:28]=[CH:27][C:13]([O:14][CH:15]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])=[CH:12][CH:11]=1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([O:14][CH:15]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([O:18][CH3:19])=[O:17])=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 19385610Methyl 2-(4-tert-butyldimethylsilyloxymethylphenoxy)-3-phenylpropanoate

Product 1

HCID 19385635Methyl 2-(4-hydroxymethylphenoxy)-3-phenylpropanoateYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.520 g (1.30 mmol) of the product of Step C dissolved in 3 mL of anhydrous TEF was added 1.3 mL (1.3 mmol) of a 1N solution of tetra-n-butylammonium fluoride in THF and the mixture was stirred at room temperature 1.5 hours. The mixture was then concentrated in vacuo and the residue was purified on a silica gel flash chromatography column eluted with 70% ethyl acetate/hexane to afford 0.230 g (62%) of the title compound.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customthe residue was purified on a silica gel flash chromatography column
  3. washeluted with 70% ethyl acetate/hexane

Sources & evidence

ORD record
ord-25a8987739e1489cb476bd2e771794a0
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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