Methanol → 4-(2-THIENYL)BENZYLAMINE

HRID 1007155노트

반응식

HRID 1007155 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO>O1CCCC1.ClCCl>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][CH:7]=1

참가 물질

6

반응물 3

HCID 887MethanolHCID 35641934-(2-thienyl)benzonitrileHCID 21226445Aluminium lithium hydride2회

생성물 1

HCID 27763324-(2-THIENYL)BENZYLAMINE수율 89%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

The 4-(2-thienyl)benzonitrile (0.086 g, 0.464 mmol) was dissolved in dry tetrahydrofuran (1.6 ml) before lithium aluminum hydride (0.46 ml, 0.464 mmol, 1 M in THF) was added dropwise. The reaction was allowed to stir at room temperature overnight. TLC (5% methanol in dichloromethane) still showed starting material remaining. Another 1 eq of LAH was added. After an additional hour, the reaction was quenched by the Fieser and Fieser method using wager (17.46 μl), aqueous sodium hydroxide solution (17.46 μl, 15% soln.), and water (52.37 μl) added sequentially to the reaction. The reaction was then diluted with diethyl ether and water and extracted twice with diethyl ether before drying over sodium sulfate and concentrating in vacuo. The residue was carried on crude without any further purification. Yield=89%.

후처리

  1. additionwas added dropwise
  2. waitAfter an additional hour
  3. customthe reaction was quenched by the Fieser and Fieser method
  4. additionadded sequentially to the reaction
  5. additionThe reaction was then diluted with diethyl ether and water
  6. extractionextracted twice with diethyl ether
  7. dry with materialbefore drying over sodium sulfate
  8. concentrationconcentrating in vacuo
  9. customThe residue was carried on crude without any further purification

출처 및 근거

ORD 기록
ord-168e996253d247ee803d963876708fb8
출처 데이터셋
uspto-grants-2004_09
특허 번호
US06794390B2

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