Ethyl Acetate → Tert-butyl(4-chloro-2-ethynylphenoxy)acetate

HRID 2390106

Reaction equation

HRID 2390106 reaction equation
[C:1]([O:5][C:6](=[O:22])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[C:17][Si](C)(C)C)([CH3:4])([CH3:3])[CH3:2].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>C1COCC1>[C:1]([O:5][C:6](=[O:22])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[CH:17])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 56594380Tert-butyl{4-chloro-2-[(trimethylsilyl)ethynyl]phenoxy}acetate2×

Product 1

HCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl{4-chloro-2-[(trimethylsilyl)ethynyl]phenoxy}acetate (Intermediate 2, 17.70 g; 52.2 mmol) in THF (180 mL) was treated with tetrabutylammonium fluoride trihydrate (16.48 g; 52.2 mmol). The reaction mixture was stirred for 4 hours, then ethyl acetate (450 mL) was added and the organic phase was washed with water (750 mL) then with brine (750 mL), dried over MgSO4, filtered and concentrated under vacuum to give a brown oily residue which was purified by flash chromatography (silica) eluting with cyclohexane containing increasing amounts of ethyl acetate. The title compound was obtained as a brown oil which solidified after prolonged standing.

Workup

  1. washthe organic phase was washed with water (750 mL)
  2. dry with materialwith brine (750 mL), dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto give a brown oily residue which
  6. customwas purified by flash chromatography (silica)
  7. washeluting with cyclohexane containing
  8. temperatureincreasing amounts of ethyl acetate

Sources & evidence

ORD record
ord-b18812189ce24d5c8731b2516ed810b4
Source dataset
uspto-grants-2012_09
Patent number
US08273769B2

Linked notes

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