Potassium tert-butoxide → 5-(3-Bromophenyl)-5-methylmorpholin-3-one

HRID 221663노트

반응식

HRID 221663 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:12][C:13](=[O:16])[CH2:14]Cl)([CH3:11])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([CH3:11])[NH:12][C:13](=[O:16])[CH2:14][O:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 23665647Potassium tert-butoxideHCID 58155284N-[1-(3-Bromophenyl)-2-hydroxy-1-methylethyl]-2-chloroacetamide

생성물 1

HCID 581553055-(3-Bromophenyl)-5-methylmorpholin-3-one

시약·촉매·용매 1

HCID 6386tert-Butanol용매

실험 절차

The crude N-[1-(3-bromo-phenyl)-2-hydroxy-1-methyl-ethyl]-2-chloro-acetamide (70 g, 230 mmol) was dissolved in tert-butanol (1 l). The solution was treated with portions of potassium tert-butoxide (52 g, 460 mmol). The mixture was refluxed for 30 min, after cooling quenched with water and evaporated. The residue was dissolved in EtOAc (500 ml) and washed with water and brine. The organic phase was dried with Na2SO4 and concentrated in vacuo to yield the crude title compound. The crude product was purified by chromatography on silica gel (PE/EtOAc=20:1 to 1:1) to give the title compound in the form of a grey solid. 1H-NMR (400 MHz, DMSO-d6): 8.66 (s, 1H), 7.60 (s, 1H), 7.48 (d, 1H), 7.44 (d, 1H), 7.34 (t, 1H), 4.02 (s, 2H), 3.92 (d, 1H), 3.68 (d, 1H), 1.38 (s, 3H).

후처리

  1. temperatureThe mixture was refluxed for 30 min
  2. temperatureafter cooling
  3. customquenched with water
  4. customevaporated
  5. dissolutionThe residue was dissolved in EtOAc (500 ml)
  6. washwashed with water and brine
  7. dry with materialThe organic phase was dried with Na2SO4
  8. concentrationconcentrated in vacuo
  9. customto yield the crude title compound
  10. customThe crude product was purified by chromatography on silica gel (PE/EtOAc=20:1 to 1:1)

출처 및 근거

ORD 기록
ord-086b51c2fe8b40fb9c46b7832f05b789
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207164B2

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