Diisobutylaluminumhydride → HCID 83478954, compound

HRID 931113Notes

Reaction equation

HRID 931113 reaction equation
[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([C:9](N(OC)C)=[O:10])[N:8]=2)[CH2:3][CH2:2]1.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([CH:9]=[O:10])[N:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 89853822HCID 89853822, compound

Product 1

HCID 83478954HCID 83478954, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-cyclopropyl-N-methoxy-N-methyloxazole-4-carboxamide (0.102 g, 0.52 mmol) in dry dichloromethane (15 mL) was added diisobutylaluminum hydride (1M in toluene) (1.04 ml, 1.04 mmol) at −78° C. The reaction mixture was stirred at −78° C. for 45 minutes. The reaction mixture was quenched with aqueous sodium hydroxide (2M) and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford 2-cyclopropyloxazole-4-carbaldehyde which was used without further purification. (65 mg) MS (API-ES+) (M+H) 138.2.

Workup

  1. customThe reaction mixture was quenched with aqueous sodium hydroxide (2M)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-41972a94cafa4f8aa30b1f911f31ce02
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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