Cesium carbonate → Methyl 4-nitrobenzyl ether

HRID 642965노트

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HRID 642965 반응식
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)(=O)=O.[O:18]1[CH2:23]COC[CH2:19]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCCCCCC.O>[CH3:19][O:18][CH2:23][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1

참가 물질

8

반응물 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 80271Tri-o-tolylphosphineHCID 5498704-Nitrophenyl trifluoromethanesulfonate

생성물 1

HCID 316176Methyl 4-nitrobenzyl ether수율 68%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매2회HCID 8900Heptane용매

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온도
95 °C

실험 절차

To a mixture of 4-nitrophenyl trifluoromethanesulfonate (30 mg, 0.11 mmol) and 1,4-dioxane (3 ml) were added water (0.3 ml), cesium carbonate (0.11 g, 0.34 mmol), potassium methoxymethyl trifluoroborate (17 mg, 0.11 mmol),palladium (II) acetate (1.3 mg, 0.0056 mmol) and tri-o-tolylphosphine (8.5 mg, 0.028 mmol). Then, the reaction mixture was stirred at 95° C. (external temperature) for 4 hours. After the reaction mixture was cooled at room temperature, water and heptane were added to the mixture, and the organic layer was separated. The organic layer was filtered, and the solvent was distilled off under reduced pressure. The residue was purified by NH-silica gel column chromatography (heptane:ethyl acetate=10:1) to obtain the title compound (13 mg, 0.078 mmol, 68%).

후처리

  1. temperatureAfter the reaction mixture was cooled at room temperature
  2. customthe organic layer was separated
  3. filtrationThe organic layer was filtered
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by NH-silica gel column chromatography (heptane:ethyl acetate=10:1)

출처 및 근거

ORD 기록
ord-6fab8db13c6e43bcb669e4b6e7648165
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696347B2

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