Aluminium lithium hydride → HCID 70354152, compound

HRID 1906771Notes

Reaction equation

HRID 1906771 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][CH2:23][CH2:24][C:25](OC)=[O:26])=[C:10]1[C:29]([O:31][CH2:32][CH3:33])=[O:30].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH3:19])[NH:12][C:11]([CH2:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])=[C:10]1[C:29]([O:31][CH2:32][CH3:33])=[O:30]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 70353565HCID 70353565, compound

Product 1

HCID 70354152HCID 70354152, compoundYield 59.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 4-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyrid-2-yl]methoxy}butanoate (0.50 g) in tetrahydrofuran (10 ml) was added dropwise over 10 minutes to a stirred, ice-cooled suspension of lithium aluminium hydride (76 mg) in tetrahydrofuran (25 ml). The mixture was stirred at 0° for 70 minutes, quenched by pouring into excess iced-water and partitioned between ethyl acetate and water. The layers were separated and the organic layer was washed twice with water, dried (MgSO4) and evaporated. The residue was purified by chromatography on silica (7 g) using dichloromethane plus 0→20% v/v ethyl acetate as the eluant. Appropriate fractions were combined and evaporated and the residue was recrystallised from diisopropyl ether to give the title compound, (0.28 g), m.p. 103°-104°.

Workup

  1. temperaturecooled
  2. customquenched
  3. additionby pouring into excess iced-water
  4. custompartitioned between ethyl acetate and water
  5. customThe layers were separated
  6. washthe organic layer was washed twice with water
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was purified by chromatography on silica (7 g)
  10. customevaporated
  11. customthe residue was recrystallised from diisopropyl ether

Sources & evidence

ORD record
ord-7b2b0b59e9074254a19c70985bcf4efe
Source dataset
uspto-grants-1987_03
Patent number
US04654353

Reaction notes

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