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

HRID 657687

反応式

HRID 657687 の反応式
[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

参加物

5

反応物 3

HCID 20155alpha-EthynylbenzenemethanolHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-28808743b7374d32ab837e9a851b7967
出典データセット
uspto-grants-2011_12
特許番号
US08076344B2

関連ノート

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