Tetrahydrofuran → 2-(8-Phenyloctyl)benzaldehyde

HRID 2258281ノート

反応式

HRID 2258281 の反応式
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=NC(C)(C)C.[Li]CCCC.Cl[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[O:33]1CCCC1>>[C:27]1([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH:1]=[O:33])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

参加物

5

反応物 4

HCID 8028Tetrahydrofuran2 回HCID 5224107-Phenyl-1-heptyl chlorideHCID 10866848HCID 10866848、化合物HCID 178418339Butyllithium

生成物 1

HCID 98176132-(8-Phenyloctyl)benzaldehyde

反応条件

温度
50 °C

実験手順

To a stirred solution of N-[(2-methylphenyl)methylene]-1,1-dimethylethanamine (21.0 g, 0.12 mol) in tetrahydrofuran (75 mL), n-BuLi (1.54M, 78 mL, 0.12 mol) was added over 1 h such that the temperature was maintained between 20°-30° C. with cooling. The mixture was stirred for 30 min and 1-chloro-7-phenylheptane (21.05 g, 0.1 mol) in tetrahydrofuran (40 mL) was added quickly. The mixture was heated at 50° C. for 3 h and quenched by the slow addition of dilute hydrochloric acid. Hydrolysis was completed by heating the mixture at 50°-60° C. for 2.5 h. The mixture was cooled to ambient temperature and the organic phase separated. The aqueous phase was extracted with hexane, and the combined organic extracts were washed with water. The extracts were dried over magnesium sulphate and, after filtering and washing the filter cake with hexane, the organic solution was concentrated under vacuum to give 2-(8-phenyloctyl)benzaldehyde as an oil (34.56 g, 65.3% pure by HPLC assay, 77% corrected yield).

後処理

  1. temperaturewas maintained between 20°-30° C.
  2. temperaturewith cooling
  3. customquenched by the slow addition of dilute hydrochloric acid
  4. customHydrolysis
  5. temperatureby heating the mixture at 50°-60° C. for 2.5 h
  6. temperatureThe mixture was cooled to ambient temperature
  7. customthe organic phase separated
  8. extractionThe aqueous phase was extracted with hexane
  9. washthe combined organic extracts were washed with water
  10. dry with materialThe extracts were dried over magnesium sulphate
  11. filtrationafter filtering
  12. washwashing the filter cake with hexane
  13. concentrationthe organic solution was concentrated under vacuum
  14. customto give

出典と根拠

ORDレコード
ord-f28a481d9c56436698f780293eaca7d8
出典データセット
uspto-grants-1997_08
特許番号
US05659084

反応ノート

読み込み中…