Aluminium lithium hydride → HCID 13822360, compound

HRID 980814Notes

Reaction equation

HRID 980814 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-d382fe122fcd4388bf17b65049e6ad12
Source dataset
uspto-grants-1987_01
Patent number
US04639442

Reaction notes

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