Aluminium lithium hydride → HCID 72996032, compound

HRID 2378518Notes

Reaction equation

HRID 2378518 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][CH:8]([CH2:13][CH:14]=[CH:15][CH2:16][CH:17]([CH3:22])[C:18](OC)=[O:19])[C:9](OC)=[O:10]>C1COCC1>[CH3:22][CH:17]([CH2:16][CH:15]=[CH:14][CH2:13][CH:8]([CH3:7])[CH2:9][OH:10])[CH2:18][OH:19]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 71332292HCID 71332292, compound

Product 1

HCID 72996032HCID 72996032, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of LiAlH4 (1.64 g, 41.0 mmol) in THF (65 mL) was added a solution of the dimethyl ester (C) (4.67 g, 20.5 mmol) in THF (15 mL) at 0° C. The mixture was stirred at that temperature for 30 min, and warmed up and stirred at room temperature for 1 h. The reaction mixture was quenched with 5% NaOH solution, extracted with Et2O thoroughly, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by SiO2 flash column chromatography (hexanes:EtOAc=2:1) to give the diol (D) (3.53 g, 20.5 mmol) in 100% yield.

Workup

  1. temperaturewarmed up
  2. stirringstirred at room temperature for 1 h
  3. customThe reaction mixture was quenched with 5% NaOH solution
  4. extractionextracted with Et2O thoroughly
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by SiO2 flash column chromatography (hexanes:EtOAc=2:1)

Sources & evidence

ORD record
ord-92f8097712e847c2be54c0a470e3697b
Source dataset
uspto-grants-2008_12
Patent number
US07470822B2

Reaction notes

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