Cesium carbonate → Methyl 4-nitrobenzyl ether

HRID 642965ノート

反応式

HRID 642965 の反応式
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

参加物

8

反応物 4

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

生成物 1

HCID 316176Methyl 4-nitrobenzyl ether収率 68%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒2 回HCID 8900Heptane溶媒

反応条件

温度
95 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-6fab8db13c6e43bcb669e4b6e7648165
出典データセット
uspto-grants-2010_04
特許番号
US07696347B2

反応ノート

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