Cesium fluoride → Methyl 2-ethynylbenzoate

HRID 424796

反応式

HRID 424796 の反応式
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[C:11][Si](C)(C)C.[F-].[Cs+]>C(#N)C.O>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[CH:11]

参加物

4

反応物 2

HCID 25953Cesium fluorideHCID 11053512Methyl 2-((trimethylsilyl)ethynyl)benzoate

生成物 1

HCID 373287Methyl 2-ethynylbenzoate収率 96.3%

試薬・触媒・溶媒 1

HCID 18373917Acetonitrile--water (1/1)溶媒

実験手順

To a solution of 2-trimethylsilanylethynyl-benzoic acid methyl ester (540 mg, 2.32 mmol) in acetonitrile/water (20 mL/5 mL) is added cesium fluoride (1.41 g, 9.30 mmol). The reaction is stirred at room temperature. After 4 h, the reaction is concentrated and the residue is partitioned between EtOAc (100 mL) and 0.2N HCl (30 mL). The aqueous layer is extracted with EtOAc (100 mL) and the combined organic layers are washed with brine, dried (MgSO4), filtered, and concentrated. The residue is chromatographed eluting with 0 to 5% EtOAc/Hexanes to yield the title compound (358 mg, 96%). GC/MS: 160.

後処理

  1. concentrationthe reaction is concentrated
  2. customthe residue is partitioned between EtOAc (100 mL) and 0.2N HCl (30 mL)
  3. extractionThe aqueous layer is extracted with EtOAc (100 mL)
  4. washthe combined organic layers are washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is chromatographed
  9. washeluting with 0 to 5% EtOAc/Hexanes

出典と根拠

ORDレコード
ord-b2bc4d24489c4b2ca44e931528859e18
出典データセット
uspto-grants-2012_01
特許番号
US08106077B2

関連ノート

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