Sulfuric Acid → 4-(2-Cyclopropyl-1,3-oxazol-4-yl)benzaldehyde

HRID 2251568Notes

Reaction equation

HRID 2251568 reaction equation
[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([C:9]3[CH:16]=[CH:15][C:12]([C:13]#N)=[CH:11][CH:10]=3)[N:8]=2)[CH2:3][CH2:2]1.CC(C[AlH]CC(C)C)C.[OH:26]S(O)(=O)=O>C(Cl)Cl>[CH:1]1([C:4]2[O:5][CH:6]=[C:7]([C:9]3[CH:16]=[CH:15][C:12]([CH:13]=[O:26])=[CH:11][CH:10]=3)[N:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14487Diisobutylaluminum hydrideHCID 69099717HCID 69099717, compound

Product 1

HCID 596432084-(2-Cyclopropyl-1,3-oxazol-4-yl)benzaldehydeYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a 0C solution of 4-(2-cyclopropyl-1,3-oxazol-4-yl)benzonitrile (0.984 g, 4.68 mmol) in anhydrous CH2Cl2 (3 ml) was added dropwise a 1M solution of DIBAL in CH2Cl2 (5.60 ml, 1.22 mmol). Upon completion of addition, the solution was warmed to 45C for 3 h. The solution was cooled and 10% aqueous H2SO4 was slowly added until pH<4. The mixture was stirred overnight at rt. The aqueous phase was extracted with CH2Cl2 (3×40 ml). The combined organic phases were dried with MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (EtOAc/hexanes, 1:4) to yield the title compound as a yellow solid (0.92 g, 92%).

Workup

  1. additionUpon completion of addition
  2. temperatureThe solution was cooled
  3. extractionThe aqueous phase was extracted with CH2Cl2 (3×40 ml)
  4. dry with materialThe combined organic phases were dried with MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by flash chromatography (EtOAc/hexanes, 1:4)

Sources & evidence

ORD record
ord-bdc1e0263f814ab5aab0c95a95e24f7f
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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