Tetrabutylammonium Fluoride → Methyl [4-(4-hydroxymethyl-3-isopropyl-phenylethynyl)-phenyl]-acetate

HRID 841497Notes

Reaction equation

HRID 841497 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](C)(C)[O:20][SiH2]C(C)(C)C)=[C:15]([CH:28]([CH3:30])[CH3:29])[CH:14]=2)=[CH:7][CH:6]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH3:1][O:2][C:3](=[O:31])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][OH:20])=[C:15]([CH:28]([CH3:29])[CH3:30])[CH:14]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131722722Methyl {4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-3-isopropyl-phenylethynyl]-phenyl}-acetate2×

Product 1

HCID 86585933Methyl [4-(4-hydroxymethyl-3-isopropyl-phenylethynyl)-phenyl]-acetateYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl{4-[4-(tert-butyl-dimethyl-silanyloxymethyl)-3-isopropyl-phenylethynyl]-phenyl}-acetate (Intermediate 154, 288.0 mg, 0.66 mmol) in 5 mL THF at 0° C. was added tetrabutylammonium fluoride (471.0 mg, 1.80 mmols; 1.8 mL of a 1M solution in THF). The pale-yellow solution was stirred for 15 minutes and quenched by the addition of ice cold H2O. The mixture was extracted with Et2O and the combined organic layers were washed with H2O and saturated aqueous NaCl before being dried (Na2SO4) and concentrated under reduced pressure. Column chromatography (5-10% EtOAc-hexanes) afforded 180.0 mg (85%) of the title compound as a colorless solid.

Workup

  1. customquenched by the addition of ice cold H2O
  2. extractionThe mixture was extracted with Et2O
  3. washthe combined organic layers were washed with H2O and saturated aqueous NaCl
  4. dry with materialbefore being dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fd53a71d78e14235bdc65ab47586380e
Source dataset
uspto-grants-2002_04
Patent number
US06369225B1

Reaction notes

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