Cesium fluoride → Methyl 2-ethynylbenzoate

HRID 424796

반응식

HRID 424796 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 373287Methyl 2-ethynylbenzoate수율 96.3%

시약·촉매·용매 1

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

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b2bc4d24489c4b2ca44e931528859e18
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106077B2

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