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

HRID 2390106노트

반응식

HRID 2390106 반응식
[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]

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 56594380Tert-butyl{4-chloro-2-[(trimethylsilyl)ethynyl]phenoxy}acetate2회

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b18812189ce24d5c8731b2516ed810b4
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273769B2

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