alpha-Ethynylbenzenemethanol → Methyl 2-(1-phenylprop-2-ynyloxy)acetate

HRID 657687

Reaktionsgleichung

Reaktionsgleichung von HRID 657687
[H-].[Na+].[C:3]1([CH:9]([OH:12])[C:10]#[CH:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:14][C:15]([O:17][CH3:18])=[O:16]>CN(C)C=O>[C:3]1([CH:9]([O:12][CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:10]#[CH:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

5

Edukt 3

HCID 20155alpha-EthynylbenzenemethanolHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate

Produkt 1

HCID 86662136Methyl 2-(1-phenylprop-2-ynyloxy)acetateAusbeute 41,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a stirred suspension of NaH (60%, 76 mg, 1.89 mmol) in 5 mL of anhydrous N,N-dimethylformamide was added 1-phenylprop-2-yn-1-ol (250 mg, 1.89 mmol). After 15 min at room temperature, methyl bromoacetate (179 μL, 1.89 mmol) was added. The resulting mixture was stirred at room temperature for 90 min before it was quenched with saturated ammonium chloride and extracted with ethyl acetate (2×15 mL). The combined organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuuo. The residue was purified by flash chromatography oh silica gel, eluting with ethyl acetate:hexane (1:9), to provide the title compound as a colorless oil (160 mg, 41% yield).

Aufarbeitung

  1. customwas quenched with saturated ammonium chloride
  2. extractionextracted with ethyl acetate (2×15 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuuo
  7. customThe residue was purified by flash chromatography oh silica gel
  8. washeluting with ethyl acetate:hexane (1:9)

Quellen und Nachweise

ORD-Eintrag
ord-28808743b7374d32ab837e9a851b7967
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076344B2

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