Tetrabutylammonium Fluoride → 3-[4-Hydroxy-2-(4-trifluoromethylphenoxymethyl)phenyl]propionic acid tert-butyl ester

HRID 1181126Notes

Reaction equation

HRID 1181126 reaction equation
[C:1]([O:5][C:6](=[O:45])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:11][C:10]=1[CH2:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][CH:36]=1)([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]([O:5][C:6](=[O:45])[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH2:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]([F:43])([F:44])[F:42])=[CH:37][CH:36]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 589792643-[4-(Tert-butyldiphenylsilanyloxy)-2-(4-trifluoromethylphenoxymethyl)phenyl]propionic acid tert-butyl ester

Product 1

HCID 589790123-[4-Hydroxy-2-(4-trifluoromethylphenoxymethyl)phenyl]propionic acid tert-butyl esterYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 100 mL round bottomed flask was charged with 3-[4-(tert-butyldiphenylsilanyloxy)-2-(4-trifluoromethylphenoxymethyl)phenyl]propionic acid tert-butyl ester (0.65 g, 1.02 mmol), anhydrous THF (40 mL), and then tetrabutylammonium fluoride (3.1 mL, 3.1 mmol, 1.0 M in THF). The reaction was stirred under a nitrogen atmosphere for 1.5 h and was concentrated. The residue was diluted with EtOAc (100 mL). The organic layer was washed with brine (2×), dried (Na2SO4), and concentrated to an orange oil. The crude oil was purified using radial chromatography (EtOAc:hexanes 15:85) to give a white solid (0.31 g, 77%). MS (ES) m/e 395 (M−1).

Workup

  1. concentrationwas concentrated
  2. additionThe residue was diluted with EtOAc (100 mL)
  3. washThe organic layer was washed with brine (2×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated to an orange oil
  6. customThe crude oil was purified

Sources & evidence

ORD record
ord-75533888dbe54ea1b574ca6d59c3aa91
Source dataset
uspto-grants-2007_10
Patent number
US07282501B2

Reaction notes

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