Diisopropylamine → Methyl 1-(2-benzyloxyphenyl)methylcyclohexan-1-carboxylate

HRID 256414

反応式

HRID 256414 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[CH:13]1([C:19]([O:21][CH3:22])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[CH2:23]([O:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33]Cl)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1>[CH2:23]([O:30][C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33][C:13]1([C:19]([O:21][CH3:22])=[O:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

参加物

6

反応物 4

HCID 7912DiisopropylamineHCID 20748Methyl cyclohexanecarboxylateHCID 5635071-(Benzyloxy)-2-(chloromethyl)benzeneHCID 178418339Butyllithium

生成物 1

HCID 13728733Methyl 1-(2-benzyloxyphenyl)methylcyclohexan-1-carboxylate収率 70%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

Under anhydrous conditions and a nitrogen atmoshere a solution of 8.7 g (0.086 mole) diisopropylamine in 250 ml tetrahydrofuran was cooled to -78° C. and 1.6M n-butyllithium (53.75 ml, 0.086 mole) was added dropwise over ten minutes. The mixture was stirred for 45 minutes, allowed to warm to 0° C. and 12.2 g (0.086 mole) methyl cyclohexancarboxylate was added. Stirring was continued for 45 minutes and then 20 g (0.086 mole) 2-benzyloxybenzyl chloride in 20 ml tetrahydrofuran was added dropwise. The resulting mixture was stirred at room temperature for 24 hours, quenched by addition of 150 ml 3M acetic acid and stirred at room temperature for one week. The mixture was diluted with ethyl ether, washed with sodium bicarbonate solution, brine, dried (MgSO4) and concentrated to a yellow oil, 29.3 g. This was distilled to obtain 20.23 g (70%) of viscous oil, b.p. 135°-140° C. (0.4 Torr).

後処理

  1. temperatureto warm to 0° C.
  2. stirringStirring
  3. waitwas continued for 45 minutes
  4. stirringThe resulting mixture was stirred at room temperature for 24 hours
  5. customquenched by addition of 150 ml 3M acetic acid
  6. stirringstirred at room temperature for one week
  7. additionThe mixture was diluted with ethyl ether
  8. washwashed with sodium bicarbonate solution, brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated to a yellow oil, 29.3 g
  11. distillationThis was distilled

出典と根拠

ORDレコード
ord-dc46a167edc14bad933bc94d43fa7b1f
出典データセット
uspto-grants-1987_10
特許番号
US04703052

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