Diisobutylaluminum hydride → HCID 54162163, compound

HRID 280094Notes

Reaction equation

HRID 280094 reaction equation
CC(C[AlH]CC(C)C)C.[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([Si:18]([CH3:26])([CH3:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:12]=1[CH:27]=[CH:28][C:29](OCC)=[O:30]>C1(C)C=CC=CC=1>[CH3:10][C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([Si:18]([CH3:26])([CH3:25])[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:12]=1[CH:27]=[CH:28][CH2:29][OH:30]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 54013261HCID 54013261, compound

Product 1

HCID 54162163HCID 54162163, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 1M solution of DIBAL in toluene (8.6 ml) was added slowly to the ester product of step (t) above (0.967 g, 2.86 mmol) in 5 ml of toluene at -78°. The reaction was stirred 4 hours with slow warming to 0°. The reaction was then re-cooled (-40°) and quenched with saturated aqueous sodium sulfate. Solid sodium sulfate and celite were added and the mixture was diluted with MTBE, stirred 10 minutes, and then filtered. The filtrate was concentrated to give 0.97 g of a clear oil which was chromatographed on silica gel (230-400 mesh) using a 3"×6.5" column with a 3:1 mixture of hexane and ethyl acetate as the eluent; 602 mg (71%) of refined alcohol product of this step was obtained.

Workup

  1. temperaturewith slow warming to 0°
  2. temperatureThe reaction was then re-cooled (-40°)
  3. customquenched with saturated aqueous sodium sulfate
  4. additionSolid sodium sulfate and celite were added
  5. additionthe mixture was diluted with MTBE
  6. stirringstirred 10 minutes
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d0c17aa0f2bc47eb8c98e63ff01dcf5a
Source dataset
uspto-grants-1986_05
Patent number
US04588715

Reaction notes

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