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Hydrogen Bromide → 2,2,4,6-Tetramethyl-5-[4-(4-methylphenyl)piperazin-1-yl]-2,3-dihydro-1-benzofuran-7-ol

HRID 1850479
ノート
印刷プレビュー

反応式

HRID 1850479 の反応式
C[O:2][C:3]1[C:11]2[O:10][C:9]([CH3:13])([CH3:12])[CH2:8][C:7]=2[C:6]([CH3:14])=[C:5]([N:15]2[CH2:20][CH2:19][N:18]([C:21]3[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)[C:4]=1[CH3:28].Br.C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH3:12][C:9]1([CH3:13])[CH2:8][C:7]2[C:6]([CH3:14])=[C:5]([N:15]3[CH2:16][CH2:17][N:18]([C:21]4[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=4)[CH2:19][CH2:20]3)[C:4]([CH3:28])=[C:3]([OH:2])[C:11]=2[O:10]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 594850811-(7-Methoxy-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methylphenyl)piperazine

生成物 1

HCID 594849982,2,4,6-Tetramethyl-5-[4-(4-methylphenyl)piperazin-1-yl]-2,3-dihydro-1-benzofuran-7-ol収率 16.4%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

To 1-(7-methoxy-2,2,4,6-tetramethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methylphenyl)piperazine (444 mg, 1.18 mmol) synthesized in Example 62, acetic acid (7 mL) and 48% aqueous solution of hydrobromic acid (7 ml) were added, followed by stirring at 100° C. for 12 hours. After cooling to room temperature, aqueous solution of saturated sodium hydrogen carbonate was added to the mixture solution, and then the mixture solution was extracted with ethyl acetate. The extract solution was dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate 100:0-90:10) and the resulting solids were recrystallized from hexane-ethyl acetate to obtain the title compound 71.0 mg (yield 16%). Melting point was 185 to 189° C.

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture solution was extracted with ethyl acetate
  3. dry with materialThe extract solution was dried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate 100:0-90:10)
  6. customthe resulting solids were recrystallized from hexane-ethyl acetate

出典と根拠

ORDレコード
ord-c85ccda7f1834e6a8474a32b9bbb6e98
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08957069B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート