Diisobutylaluminum hydride → HCID 90456193, compound

HRID 2202092Notes

Reaction equation

HRID 2202092 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][CH:12]=[N:11][C:10]=2[C:14](OCC)=[O:15])=[CH:5][CH:4]=1)#[N:2].CC(C[AlH]CC(C)C)C>C1COCC1.C1(C)C=CC=CC=1>[CH:14]([C:10]1[N:11]=[CH:12][O:13][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)=[O:15]

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 61633471HCID 61633471, compound

Product 1

HCID 90456193HCID 90456193, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 5-(4-cyanophenyl)oxazole-4-carboxylate (500 mg, 2.06 mmol, 1.00 equiv) in anhydrous THF (10 mL) maintained under nitrogen at −78° C. was added dropwise a 25% solution of DIBAL (2.5 mL) in toluene with stirring. The resulting solution was stirred at −40° C. for 3 h and then quenched by the addition of 10 mL of water. The mixture was extracted with 2×10 mL of ethyl acetate. The combined organic layers was washed with 1×20 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-20% of ethyl acetate in petroleum ether to yield 350 mg (86%) of 4-(4-formyloxazol-5-yl)benzonitrile as a yellow solid. 1H-NMR (300 MHz, CDCl3): δ 10.16 (s, 1H), 8.42 (d, J=8.4 Hz, 2H), 8.04 (s, 1H), 7.83 (d, J=8.4 Hz, 2H) ppm.

Workup

  1. stirringThe resulting solution was stirred at −40° C. for 3 h
  2. customquenched by the addition of 10 mL of water
  3. extractionThe mixture was extracted with 2×10 mL of ethyl acetate
  4. washThe combined organic layers was washed with 1×20 mL of brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified on a silica gel column
  8. washeluted with 0-20% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-0171b010030a478aa1abc4c967ba4ccc
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

Loading…