Ethylene Oxide → 4-[7-(2-Hydroxyethyl)-3-isoquinolinyl]benzonitrile

HRID 551553ノート

反応式

HRID 551553 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[N:8]=[CH:9]2)=[CH:4][CH:3]=1.[Li]CCCC.[CH2:25]1[O:27][CH2:26]1>C1COCC1>[OH:27][CH2:26][CH2:25][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=3)[N:8]=[CH:9]2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6354Ethylene OxideHCID 671042584-(7-Bromo-3-isoquinolinyl)benzonitrileHCID 178418339Butyllithium

生成物 1

HCID 671046674-[7-(2-Hydroxyethyl)-3-isoquinolinyl]benzonitrile

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-60 °C

実験手順

The product from Example 74A (4 mmol) is dissolved in 20 mL THF and is cooled to −60° C. under nitrogen. n-BuLi (4.4 mmol) is added dropwise, and the mixture is stirred at −60° C. for additional 30 minutes. A solution of ethylene oxide (20 mmol) in 10 ml THF is added and the mixture is allowed to warm to 10° C. and is stirred to complete the reaction. The mixture is cooled back down to 0° C. and is slowly quenched with 2N HCl to pH=3. The solvent is removed under vacuum and the residue is dissolved in 20 mL methylene chloride, is washed with water, and is concentrated under reduced pressure. The residue is chromatographed on silica gel (5:95 MeOH:CHCl3) to provide the title compound.

後処理

  1. temperatureto warm to 10° C.
  2. stirringis stirred
  3. customthe reaction
  4. temperatureThe mixture is cooled back down to 0° C.
  5. customis slowly quenched with 2N HCl to pH=3
  6. customThe solvent is removed under vacuum
  7. dissolutionthe residue is dissolved in 20 mL methylene chloride
  8. washis washed with water
  9. concentrationis concentrated under reduced pressure
  10. customThe residue is chromatographed on silica gel (5:95 MeOH:CHCl3)

出典と根拠

ORDレコード
ord-3a74632a98224bdb876392fdd186aec3
出典データセット
uspto-grants-2011_05
特許番号
US07947711B2

反応ノート

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