Ammonium Chloride → HCID 58036800、化合物

HRID 1028357ノート

反応式

HRID 1028357 の反応式
[C:1]1([P:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[N:16]=[CH:15][CH:14]=[CH:13]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li][CH3:25].[NH4+].[Cl-]>C1COCC1>[C:18]1([P:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[C:12]3[C:17]=2[NH:16][CH:15]([CH3:25])[CH:14]=[CH:13]3)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 6286598-(Diphenylphosphino)quinolineHCID 178418348HCID 178418348、化合物

生成物 1

HCID 58036800HCID 58036800、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of 8-diphenylphoshinoquinoline (1) (10 g, 31.95 mmol) in dry THF (150 mL) under nitrogen was added MeLi (39.9 mL, 1.6 M in diethyl ether, 1 mmol) at −78° C. and the solution was stirred at 0° C. for 10 minutes. The solution was cooled down to −78° C., saturated aqueous NH4Cl solution (100 mL) was added and the mixture was warmed to room temperature. Products were extracted with EtOAc, washed with water and saturated aqueous NaCl, dried (MgSO4) and evaporated to give 2 as a yellow oil, which solidified on standing (10.5 g, quantitative). 1H NMR (400.13 MHz, CDCl3) δ 7.4-7.25 (m, 10H, Ph-H), 6.86 (dd, 1H, J=7.2, 1.2, C5—H), 6.63 (ddd, 1H, J=7.6, 6.0, 1.6 Hz, C7—H), 6.49 (t, 1H, J=7.6 Hz, C6—H), 6.29 (d, 1H, J=9.6 Hz, C4—H), 5.54 (ddd, 1H, J=10.0, 4.0, 2.0 Hz, C3—H), 4.71 (d, 1H, J=7.6 Hz, N1—H), 4.35 (m, 1H, C2—H), 1.15 (d, 3H, J=6.4 Hz, C1′—CH3) ppm; 13C NMR (100.61 MHz, CDCl3) δ 147.0 (d, J=18.2 Hz), 135.5 (d, J=13.1 Hz), 135.4 (d, J=12.1 Hz), 134.2 (d, J=5.1 Hz), 133.4 (d, J=18.2 Hz), 133.3 (d, J=18.2 Hz), 128.5 (d, J=11.1 Hz), 128.4 (d, J=12.1 Hz), 128.0, 117.0, 116.1, 48.2, 24.2 ppm; 31P NMR (161.97 MHz, CDCl3) δ −23.2 ppm.

後処理

  1. temperatureThe solution was cooled down to −78° C.
  2. temperaturethe mixture was warmed to room temperature
  3. extractionProducts were extracted with EtOAc
  4. washwashed with water and saturated aqueous NaCl
  5. dry with materialdried (MgSO4)
  6. customevaporated

出典と根拠

ORDレコード
ord-34373df281ed49f69a10ae01bd9cd71b
出典データセット
uspto-grants-2014_05
特許番号
US08735583B2

反応ノート

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