Ethyl Acetate → Tert-butyl(4-chloro-2-ethynylphenoxy)acetate

HRID 2390106

反応式

HRID 2390106 の反応式
[C:1]([O:5][C:6](=[O:22])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[C:17][Si](C)(C)C)([CH3:4])([CH3:3])[CH3:2].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>C1COCC1>[C:1]([O:5][C:6](=[O:22])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]#[CH:17])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 56594380Tert-butyl{4-chloro-2-[(trimethylsilyl)ethynyl]phenoxy}acetate2 回

生成物 1

HCID 56594381Tert-butyl(4-chloro-2-ethynylphenoxy)acetate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of tert-butyl{4-chloro-2-[(trimethylsilyl)ethynyl]phenoxy}acetate (Intermediate 2, 17.70 g; 52.2 mmol) in THF (180 mL) was treated with tetrabutylammonium fluoride trihydrate (16.48 g; 52.2 mmol). The reaction mixture was stirred for 4 hours, then ethyl acetate (450 mL) was added and the organic phase was washed with water (750 mL) then with brine (750 mL), dried over MgSO4, filtered and concentrated under vacuum to give a brown oily residue which was purified by flash chromatography (silica) eluting with cyclohexane containing increasing amounts of ethyl acetate. The title compound was obtained as a brown oil which solidified after prolonged standing.

後処理

  1. washthe organic phase was washed with water (750 mL)
  2. dry with materialwith brine (750 mL), dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customto give a brown oily residue which
  6. customwas purified by flash chromatography (silica)
  7. washeluting with cyclohexane containing
  8. temperatureincreasing amounts of ethyl acetate

出典と根拠

ORDレコード
ord-b18812189ce24d5c8731b2516ed810b4
出典データセット
uspto-grants-2012_09
特許番号
US08273769B2

関連ノート

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