Hexane → Methyl 2-(1-phenylprop-2-ynyloxy)acetate

HRID 1042069

Reaktionsgleichung

Reaktionsgleichung von HRID 1042069
[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].CCCCCC>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

6

Edukt 4

HCID 8058HexaneHCID 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 on 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 on silica gel
  8. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4221e7b77e3d4cd281b8b248cb8bb85d
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08557828B2

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