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

HRID 657687

Reaction equation

HRID 657687 reaction equation
[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

Participants

5

Reactant 3

HCID 20155alpha-EthynylbenzenemethanolHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate

Product 1

HCID 86662136Methyl 2-(1-phenylprop-2-ynyloxy)acetateYield 41.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-28808743b7374d32ab837e9a851b7967
Source dataset
uspto-grants-2011_12
Patent number
US08076344B2

Linked notes

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