Aluminium lithium hydride → HCID 69673993, compound

HRID 2283249Notes

Reaction equation

HRID 2283249 reaction equation
CO[C:3]1[CH:4]=[C:5]([C:9]2[N:10]=[N:11][CH:12]=[C:13]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:14]=2[C:15]2[O:16][CH:17]=[C:18]([C:20](OC)=[O:21])[N:19]=2)[CH:6]=[CH:7][CH:8]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:5]1([C:9]2[N:10]=[N:11][CH:12]=[C:13]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:14]=2[C:15]2[O:16][CH:17]=[C:18]([CH2:20][OH:21])[N:19]=2)[CH:6]=[CH:7][CH:8]=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69673559HCID 69673559, compound

Product 1

HCID 69673993HCID 69673993, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 26 (20 mg, 0.056 mmol) in THF (3 mL), LAH (5.0 mg, 0.14 mmol) was added at −30° C. and stirred for 1 h. The reaction mixture was quenched with saturated ammonium chloride solution at −30° C. The reaction mixture was slowly warmed to rt and filtered through celite bed, washed with ethyl acetate. The organic layer was washed with brine, dried over anhy. Na2SO4 and concentrated under reduced pressure to obtain the crude product gave (2-(3,5-diphenylpyridazin-4-yl)oxazol-4-yl)methanol (16 mg, 88%) as an yellow solid.

Workup

  1. customThe reaction mixture was quenched with saturated ammonium chloride solution at −30° C
  2. filtrationfiltered through celite bed
  3. washwashed with ethyl acetate
  4. washThe organic layer was washed with brine
  5. customdried over anhy
  6. concentrationNa2SO4 and concentrated under reduced pressure
  7. customto obtain the crude product

Sources & evidence

ORD record
ord-964f07997645434a9c606381ce9b6e64
Source dataset
uspto-grants-2015_09
Patent number
US09145372B2

Reaction notes

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