Diisobutylaluminum hydride → HCID 19434065, compound

HRID 1736039Notes

Reaction equation

HRID 1736039 reaction equation
[CH3:1][N:2]1[C:7]([C:8](OCC)=[O:9])=[CH:6][C:5]2[S:13][CH:14]=[CH:15][C:4]=2[S:3]1(=[O:17])=[O:16].CC(C[AlH]CC(C)C)C>C1COCC1>[CH3:1][N:2]1[C:7]([CH2:8][OH:9])=[CH:6][C:5]2[S:13][CH:14]=[CH:15][C:4]=2[S:3]1(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 19434039HCID 19434039, compound

Product 1

HCID 19434065HCID 19434065, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Step D (3.16 g, 11.6 mmol) in anhydrous THF (30 mL) at 0° C. was added DIBAL (1.0M, 29.0 mL, 29.0 mmol). This mixture was stirred for 30 min, warmed to ambient temperature, and stirred for an additional 30 min. The mixture was evaporated to dryness and the residue mixed with ethyl acetate (100 mL) and poured into 2N HCl (50 mL). The organic layer was seperated, washed with brine, dried (MgSO4) and evaporated to dryness. Column chromatography (silica, ethyl aectate/hexane) gave a viscous oil which solidified on standing: mp 78°-80° C.

Workup

  1. stirringstirred for an additional 30 min
  2. customThe mixture was evaporated to dryness
  3. additionthe residue mixed with ethyl acetate (100 mL)
  4. additionpoured into 2N HCl (50 mL)
  5. customThe organic layer was seperated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. customevaporated to dryness
  9. customColumn chromatography (silica, ethyl aectate/hexane) gave a viscous oil which

Sources & evidence

ORD record
ord-d130c21570594b3ba1b29224265f48e3
Source dataset
uspto-grants-1996_07
Patent number
US05538966

Reaction notes

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