Diethyl methylphosphonate → HCID 86691595、化合物

HRID 333945

反応式

HRID 333945 の反応式
[CH2:1]([O:3][P:4]([CH3:9])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].C([Li])CCC.[N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([N:25]2[CH2:30][CH2:29][N:28]([C:31](OCC)=[O:32])[CH2:27][CH2:26]2)=[CH:17][CH:16]=1.[OH-].[Na+]>C1COCC1.CCCCCC.O.C(O)(=O)C>[CH2:1]([O:3][P:4]([CH2:9][C:31]([N:28]1[CH2:29][CH2:30][N:25]([C:18]2[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:15]=[CH:16][CH:17]=2)[CH2:26][CH2:27]1)=[O:32])([O:5][CH2:6][CH3:7])=[O:8])[CH3:2]

参加物

9

反応物 4

HCID 12685Diethyl methylphosphonateHCID 14798Sodium HydroxideHCID 66835834HCID 66835834、化合物HCID 178418339Butyllithium

生成物 1

HCID 86691595HCID 86691595、化合物

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

Diethylmethylphosphonate (302.8 mg, 2 mmol) was dissolved in anhydrous THF (2.5 ml), the mixture was cooled to −78° C. under argon, n-butyllithium (2.11 mmol, 846 μl of a 2.5 M solution in hexane) was added dropwise with stirring. After addition was complete, stirring was continued for 20 minutes, after which ethyl 4-(4-quinolyl)piperazine-1-carboxylate (284 mg, 1 mmol) dissolved in 0.5 μl THF was added dropwise. The mixture was allowed to reach room temperature overnight with continued stirring. Glacial acetic acid (0.25 ml) and water (2 ml) was added, after which the mixture was basified with 0.1 NaOH and extracted with diethylether (2×). The organic phases were combined, washed with 5% sodium bicarbonate and water. The aqueous phases were back-extracted with diethylether after basification with 0.1 N NaOH and the combined organic phases dried over magnesium sulfate and the solvent was removed under reduced pressure to yield 271 mg (0.693 mmol, 69%). MS (ESI): m/z=392.1 [M+1]+.

後処理

  1. additionAfter addition
  2. stirringstirring
  3. additionwas added dropwise
  4. waitto reach room temperature overnight with continued stirring
  5. extractionextracted with diethylether (2×)
  6. washwashed with 5% sodium bicarbonate and water
  7. extractionThe aqueous phases were back-extracted with diethylether after basification with 0.1 N NaOH
  8. dry with materialthe combined organic phases dried over magnesium sulfate
  9. customthe solvent was removed under reduced pressure
  10. customto yield 271 mg (0.693 mmol, 69%)

出典と根拠

ORDレコード
ord-35905a4a66f54338a085c9c0a7ee01a4
出典データセット
uspto-grants-2014_11
特許番号
US08883791B2

関連ノート

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