Diisobutylaluminumhydride → HCID 21404785, compound

HRID 1729983Notes

Reaction equation

HRID 1729983 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]([CH2:13][C:14](OC)=[O:15])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[N:4]=[C:5]([CH2:13][CH:14]=[O:15])[C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 21404789HCID 21404789, compound

Product 1

HCID 21404785HCID 21404785, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To 1 part of methyl 3-methoxy-2-azanaphthaleneacetate in 25 parts by volume of toluene at -78° C is slowly added 0.33 part of diisobutylaluminum hydride in toluene. The reaction is stirred for 1 hour and allowed to come to room temperature. The reaction is quenched with ethylacetate followed by ice water. The organic layer is washed with saturated sodium chloride, dried with anhydrous sodium sulfate, and 3-methoxy-2-azanaphthaleneacetaldehyde is isolated. This compound has the following structural formula ##SPC24##

Workup

  1. customto come to room temperature
  2. customThe reaction is quenched with ethylacetate
  3. washThe organic layer is washed with saturated sodium chloride
  4. dry with materialdried with anhydrous sodium sulfate

Sources & evidence

ORD record
ord-0c46d21b34914878a7951189efe97e20
Source dataset
uspto-grants-1976_11
Patent number
US03991061

Reaction notes

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