Aluminium lithium hydride → HCID 131714671, compound

HRID 980809Notes

Reaction equation

HRID 980809 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]12[CH:23]=[CH:22][CH:21]=[CH:20][CH:9]1[CH2:10][CH:11]2[C:12]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)=O)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.CCOCC>[NH2:1][CH2:4][CH2:5][CH2:6][O:7][C:8]12[CH:23]=[CH:22][CH:21]=[CH:20][CH:9]1[CH2:10][CH:11]2[CH2:12][N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 131715043HCID 131715043, compound

Product 1

HCID 131714671HCID 131714671, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the azidobenzocyclobutenylamide compound of Step 2. above (3.2 g) in THF (20.4 ml) is added dropwise to a suspension of LAH (0.93 g) in anhydrous ether (122 ml) stirred under nitrogen maintained at ice bath temperatures. The reaction mixture is refluxed for 15 hours, cooled and quenched with water (0.93 ml), aqueous sodium hydroxide (15% solution, 0.93 ml) and water (2.79 ml) and filtered. The solid is washed with ether and the combined filtrate dried, filtered, evaporated in vacuo and chromatographed (silica gel: ethyl acetate/methanol). The pure fractions are combined and evaporated in vacuo yielding an oil, which is identified at the desired product by NMR.

Workup

  1. temperaturemaintained at ice bath temperatures
  2. temperatureThe reaction mixture is refluxed for 15 hours
  3. temperaturecooled
  4. customquenched with water (0.93 ml), aqueous sodium hydroxide (15% solution, 0.93 ml) and water (2.79 ml)
  5. filtrationfiltered
  6. washThe solid is washed with ether
  7. customthe combined filtrate dried
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customchromatographed (silica gel: ethyl acetate/methanol)
  11. customevaporated in vacuo
  12. customyielding an oil, which

Sources & evidence

ORD record
ord-b358a35fde13413cb2599df70dcafb4f
Source dataset
uspto-grants-1987_01
Patent number
US04639442

Reaction notes

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