Aluminium lithium hydride → HCID 89498460, compound

HRID 1778891Notes

Reaction equation

HRID 1778891 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C@H:5]1[C@H:10]([CH:11]=[O:12])[CH2:9][C@@H:8]2[CH2:13][C@H:6]1[C:7]2([CH3:15])[CH3:14].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][C@H:5]1[C@H:10]([CH2:11][OH:12])[CH2:9][C@@H:8]2[CH2:13][C@H:6]1[C:7]2([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86681318HCID 86681318, compound

Product 1

HCID 89498460HCID 89498460, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 150A (407 mg) in tetrahydrofuran (10 mL), which was cooled in a room temperature water bath, was added dropwise LAH (1.0M in tetrahydrofuran, 2.3 mL). The reaction was stirred at room temperature for 1 hour then quenched with water (25 mL). The resulting suspension was filtered through diatomaceous earth, and the filter cake was rinsed with ether (50 mL). The layers were separated and the aqueous layer was extracted with ether (2×25 mL). The extracts were washed with brine (25 mL), dried (MgSO4), filtered, and concentrated to give the title compound, which was used without further purification.

Workup

  1. customthen quenched with water (25 mL)
  2. filtrationThe resulting suspension was filtered through diatomaceous earth
  3. washthe filter cake was rinsed with ether (50 mL)
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with ether (2×25 mL)
  6. washThe extracts were washed with brine (25 mL)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-f6e07da376d540f3a696d1163754f2ca
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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