Diethyl Ether → HCID 66808431, compound

HRID 607246Notes

Reaction equation

HRID 607246 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl-].[Al+3].[Cl-].[Cl-].[NH2:11][C:12]1[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:13]=1[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O.C(OCC)C>O1CCCC1.O>[CH2:14]([C:13]1[CH:22]=[CH:23][C:24]([CH3:26])=[CH:25][C:12]=1[NH2:11])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 786512-Amino-4-methylbenzophenoneHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 66808431HCID 66808431, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of lithium aluminum hydride in tetrahydrofuran (1.0 M, 2.54 mL, 2.54 mmol) was added via syringe to a flask containing aluminum chloride (534 mg, 4.005 mmol) under a nitrogen atmosphere and cooled in a 0° bath. After letting the mixture cool for 5 minutes, a solution of 2-amino-4-methylbenzophenone (200 mg, 0.9467 mmol) in tetrahydrofuran (4 mL) was added slowly dropwise at 0°. The reaction was then heated at 50° for 30 minutes. The reaction was cooled to room temperature and moist ethyl ether (5 mL) was added. The reaction was carefully poured into water (20 mL) and extracted with ethyl ether (2×50 mL). The combined ethereal extracts were washed with brine (20 mL), dried over anhydrous sodium sulfate, filtered, and concentrated by rotary evaporation under vacuum. Purification by silica gel flash chromatography using 40:60 hexanes/methylene chloride as eluent provided the title compound as an oil (94 mg, 50%).

Workup

  1. temperaturecooled in a 0° bath
  2. temperaturecool for 5 minutes
  3. temperatureThe reaction was then heated at 50° for 30 minutes
  4. extractionextracted with ethyl ether (2×50 mL)
  5. washThe combined ethereal extracts were washed with brine (20 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation under vacuum
  9. customPurification by silica gel flash chromatography

Sources & evidence

ORD record
ord-a1850e16025044babe2eb9adacce0535
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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