Aluminium lithium hydride → HCID 13822360, compound

HRID 2232259Notes

Reaction equation

HRID 2232259 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:8]([CH3:17])([C:9]([N:11]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]3)=O)[CH:7]([CH3:18])[C:6]2=[CH:19][CH:20]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:17][C:8]1([CH2:9][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[C:5]2=[CH:4][C:3]([O:2][CH3:1])=[CH:20][CH:19]=[C:6]2[CH:7]1[CH3:18]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 21283384HCID 21283384, compound

Product 1

HCID 13822360HCID 13822360, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the 1,2 -dimethyl compound obtained in Step 1. above (43.8 g) in anhydrous THF (640 ml) is added dropwise to a suspension of LAH (7.6 g) in anhydrous THF (200 ml). The reaction mixture is heated to reflux for 45 minutes, cooled and quenched with water, aqueous NaOH (15%), and water. The reaction mixture is filtered, evaporated in vacuo and chromatographed (silica gel: ethyl acetate/hexane) and the major fractions combined, and evaporated yielding the desired product as an oil which is identified by NMR. The oil is dissolved in methanolic hydrochloric acid, the methanolic solution evaporated and the residue recrystallized (acetonitrile/ether), M.P.=179°-181° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 45 minutes
  3. temperaturecooled
  4. customquenched with water, aqueous NaOH (15%), and water
  5. filtrationThe reaction mixture is filtered
  6. customevaporated in vacuo
  7. customchromatographed (silica gel: ethyl acetate/hexane)
  8. customevaporated

Sources & evidence

ORD record
ord-3bfba41f94e04f508f9105fd7539979b
Source dataset
uspto-grants-1988_11
Patent number
US04788187

Reaction notes

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