Diisobutylaluminum hydride → HCID 66717571, compound

HRID 2194873Notes

Reaction equation

HRID 2194873 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH2:9][CH2:10][C:11](OCC)=[O:12].CC(C[AlH]CC(C)C)C>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[CH2:9][CH2:10][CH2:11][OH:12]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 66718108HCID 66718108, compound

Product 1

HCID 66717571HCID 66717571, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of the ester from Step 1 (1 eq.) in THF (0.07M) at −78° C. was added dropwise DIBAL-H (2.1 eq). The reaction mixture was stirred 1 h at −78° C., warm slowly to 0° C. quenched with aqueous 1N HCl and finally diluted with Et2O. The organic extract was washed with aqueous 6N HCl, water, saturated aqueous NaHCO3, brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (0 to 50%, in 30 min) afforded the desired compound.

Workup

  1. temperaturewarm slowly to 0° C.
  2. customquenched with aqueous 1N HCl
  3. additionfinally diluted with Et2O
  4. extractionThe organic extract
  5. washwas washed with aqueous 6N HCl, water, saturated aqueous NaHCO3, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by column chromatography on silica gel (Combi-Flash by ISCO)
  10. washeluting with Hex/EtOAc (0 to 50%, in 30 min)

Sources & evidence

ORD record
ord-bda90ca62361450790d208b3124fef5e
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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