Diisobutylaluminum hydride → HCID 19434093, compound

HRID 1736021Notes

Reaction equation

HRID 1736021 reaction equation
CC(C[AlH]CC(C)C)C.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:23]([C:24](OC)=[O:25])=[CH:22][C:21]3[CH:28]=[CH:29][S:30][C:20]=3[S:19]2(=[O:32])=[O:31])=[CH:14][CH:13]=1>C1COCC1>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:23]([CH2:24][OH:25])=[CH:22][C:21]3[CH:28]=[CH:29][S:30][C:20]=3[S:19]2(=[O:32])=[O:31])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 19434131HCID 19434131, compound

Product 1

HCID 19434093HCID 19434093, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A 1M solution of DIBAL in THF (45 mL, 45 mmol) was added to a solution of the product from Step C (1.92 g) in anhydrous THF (100 mL) and this mixture was stirred at ambient temperature for 18 h. After cooling (ice bath) the reaction was quenched by the addition of 1N HCl (100 mL). This mixture was extracted with ethyl acetate (2×100 mL) and the combined extracts were dried (MgSO4) and evaporated to a residue which was purified by column chromatography (silica, 50% ethyl acetate/hexane) to give a viscous oil (1.19 g, 41%).

Workup

  1. temperatureAfter cooling (ice bath) the reaction
  2. customwas quenched by the addition of 1N HCl (100 mL)
  3. extractionThis mixture was extracted with ethyl acetate (2×100 mL)
  4. dry with materialthe combined extracts were dried (MgSO4)
  5. customevaporated to a residue which
  6. customwas purified by column chromatography (silica, 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0638c323bf3d4b55bf225bf299e87f47
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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