Trimethylaluminum → HCID 86725332、化合物

HRID 925218ノート

反応式

HRID 925218 の反応式
[CH2:1]([O:3][C:4]([N:6]1[CH2:23][CH2:22][C:10]2[C:11]3[C:12](Cl)([CH3:20])[C:13]([F:19])([F:18])[CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].[CH3:24][Al](C)C>C1CCCCC1>[CH2:1]([O:3][C:4]([N:6]1[CH2:23][CH2:22][C:10]2[C:11]3[C:12]([CH3:24])([CH3:20])[C:13]([F:19])([F:18])[CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

参加物

4

反応物 2

HCID 16682925TrimethylaluminumHCID 86725330HCID 86725330、化合物

生成物 1

HCID 86725332HCID 86725332、化合物収率 9.9%

試薬・触媒・溶媒 1

HCID 8078Cyclohexane溶媒

反応条件

温度
80 °C

実験手順

Into a glass vial the product from step (b) (214 mg, 0.623 mmol) dissolved in cyclohexane (3 ml) was added. To this solution, AlMe3 (2M in hexanes, 1.2 ml, 2.49 mmol) was added. The reaction mixture was heated to 80° C. and stirred for 1 hour. The reaction mixture was allowed to cool to room temperature and was quenched by the addition of 2M HCl (20 ml). The aqueous mixture was extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the crude product. Purification by silica-gel chromatography (gradient elution: 0 to 20% EtOAc in hexanes) gave the sub-title compound as an orange oil (20 mg). NMR (300 MHz, CDCl3) δ 6.99 (s, 2H); 4.15 (q, J=7.2 Hz, 2H); 3.62-3.59 (m, 4H); 3.29 (t, J=14.1 Hz, 2H); 3.01-2.91 (m, 2H); 1.39 (s, 6H); 1.26 (t, J=7.2 Hz, 3H); MS: ESI (positive): 324 (M+1).

後処理

  1. additionwas added
  2. temperatureto cool to room temperature
  3. customwas quenched by the addition of 2M HCl (20 ml)
  4. extractionThe aqueous mixture was extracted with EtOAc (3×)
  5. washThe combined EtOAc extracts were washed with brine
  6. dry with materialdried over Na2SO4, and solvent
  7. customevaporated in vacuo
  8. customto give the crude product
  9. customPurification
  10. washby silica-gel chromatography (gradient elution: 0 to 20% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-3caf3f0b9150487ab1bd70a04c7ce2a6
出典データセット
uspto-grants-2016_03
特許番号
US09284277B2

反応ノート

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