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

Reaktionsgleichung

[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

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).