Diisobutylaluminum hydride → HCID 21880639, compound

HRID 1297076Notes

Reaction equation

HRID 1297076 reaction equation
CC(C[AlH]CC(C)C)C.C([O:12][C:13](=O)[CH2:14][CH2:15][C:16]1[S:17][C:18]([CH2:21][CH2:22][C:23](OCC)=[O:24])=[CH:19][CH:20]=1)C>C1COCC1>[OH:24][CH2:23][CH2:22][CH2:21][C:18]1[S:17][C:16]([CH2:15][CH2:14][CH2:13][OH:12])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 21880674HCID 21880674, compound

Product 1

HCID 21880639HCID 21880639, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of DIBAL (88 mL, 88 mmol, 1.0 M in cyclohexane) in THF (300 mL) was cooled to −78° C. and the intermediate from Step B (5.0 g, 17.6 mmol) was added dropwise. After complete addition, the reaction mixture was warmed to ambient temperature over 30 minutes. The reaction was then quenched by slowly adding 1N HCl (200 mL) and then DCM (400 mL) was added. The organic layer was removed and the aqueous layer was washed with DCM (4×100 mL). The combined organic layers were then washed with saturated NaCl (100 mL), dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to provide 3.0 g of the title intermediate (85% yield), which was used without further purification.

Workup

  1. additionAfter complete addition
  2. customThe reaction was then quenched
  3. additionby slowly adding 1N HCl (200 mL)
  4. additionDCM (400 mL) was added
  5. customThe organic layer was removed
  6. washthe aqueous layer was washed with DCM (4×100 mL)
  7. washThe combined organic layers were then washed with saturated NaCl (100 mL)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-d53eea509d9d4131af5a2d1cfebe2c3e
Source dataset
uspto-grants-2007_07
Patent number
US07250414B2

Reaction notes

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