Water → 2-(5-Methyl-2-thienyl)ethanamine

HRID 915653노트

반응식

HRID 915653 반응식
[CH3:1][C:2]1[S:3][C:4]([CH:7]=[CH:8][N+:9]([O-])=O)=[CH:5][CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C(OCC)C>[CH3:1][C:2]1[S:3][C:4]([CH2:7][CH2:8][NH2:9])=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 539158762-Methyl-5-(2-nitro-vinyl)-thiophene

생성물 1

HCID 147881892-(5-Methyl-2-thienyl)ethanamine수율 20.3%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

실험 절차

Add 2-methyl-5-(2-nitrovinyl)thiophene (483 mg crude, 2.855 mmol, 1 eq) as a solution in diethyl ether (15 mL) to a solution of lithium aluminum hydride (227 mg, 5.995 mmol, 2.1 eq) in diethyl ether (5.995 mL) at a rate such as to maintain gentle reflux of the solution. Stir reaction for 5 minutes. Cautiously add water followed by several small portions of potassium sodium tartrate. Stir reaction vigorously for 1 hour and then let stand overnight. Separate organics, dry with magnesium sulfate, and concentrate on rotovap to give 360 mg of crude product as an oil. Perform column chromatography to give 82 mg (20% yield) of 2-(5-methylthiophen-2-yl)ethylamine. MS (m/e): 142.0 (MH+).

후처리

  1. temperatureto maintain gentle
  2. temperaturereflux of the solution
  3. customreaction for 5 minutes
  4. stirringStir
  5. customreaction vigorously for 1 hour
  6. dry with materialSeparate organics, dry with magnesium sulfate
  7. concentrationconcentrate on rotovap
  8. customto give 360 mg of crude product as an oil

출처 및 근거

ORD 기록
ord-d4000a2965774253ad3b57b539091f4c
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07265246B2

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