Diisobutylaluminum hydride → 5-(4-Chlorophenyl)oxazole-4-carbaldehyde

HRID 1506661Notes

Reaction equation

HRID 1506661 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][CH:11]=[N:10][C:9]=2[C:13](OCC)=[O:14])=[CH:4][CH:3]=1.CC(C[AlH]CC(C)C)C.[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][CH:11]=[N:10][C:9]=2[CH:13]=[O:14])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14487Diisobutylaluminum hydrideHCID 25517Ammonium ChlorideHCID 2739479Ethyl 5-(4-chlorophenyl)oxazole-4-carboxylate

Product 1

HCID 153155355-(4-Chlorophenyl)oxazole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 33C (1.25 g, 5 mmol) in THF was added DIBAL-H (1.0 M in toluene, 10 mmol) dropwise at −70° C. The resulting solution was allowed to warm to −20° C. over 3 h. Upon completion of the reaction, saturated aqueous NH4Cl was added to the flask and the mixture was partitioned between EtOAc and water. The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was used in the next step without further purification. MS (m/z) 208.1 [M+H]+.

Workup

  1. additionwas added to the flask
  2. customthe mixture was partitioned between EtOAc and water
  3. washThe organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was used in the next step without further purification

Sources & evidence

ORD record
ord-87a12a81f3ff4951aaca26b829b1799c
Source dataset
uspto-grants-2015_12
Patent number
US09220710B2

Reaction notes

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