HCID 18174725, compound → HCID 10934578, compound

HRID 563060Notes

Reaction equation

HRID 563060 reaction equation
[Cl:1][C:2]1[O:3][C:4]([CH2:14][CH2:15][C:16](OCC)=[O:17])=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=2)[N:6]=1.[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1.C1(C)C=CC=CC=1>[Cl:1][C:2]1[O:3][C:4]([CH2:14][CH2:15][CH2:16][OH:17])=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=2)[N:6]=1

Participants

5

Reactant 2

HCID 18174725HCID 18174725, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 10934578HCID 10934578, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Ethyl 2-chloro-4-(4-chlorophenyl)-5-oxazolepropionate (9.00 g) was dissolved in tetrahydrofuran (100 ml), the solution was cooled to −78° C., and a 1 N solution of diisobutylaluminum hydride in toluene (65 ml) was added dropwise with stirring. After completion of the dropping, the cooling bath was removed to raise the inner temperature to −20° C. Sodium sulfate decahydrate (10.0 g) was added to the reaction mixture, and the temperature was raised to room temperature. The reaction mixture was filtered, and the residue on the filter paper was washed with ethyl acetate. The filtrate was concentrated to give crystals of 2-chloro-4-(4-chlorophenyl)-5-oxazolepropanol (7.00 g, 86%).

Workup

  1. customAfter completion of the dropping, the cooling bath was removed
  2. temperatureto raise the inner temperature to −20° C
  3. additionSodium sulfate decahydrate (10.0 g) was added to the reaction mixture
  4. temperaturethe temperature was raised to room temperature
  5. filtrationThe reaction mixture was filtered
  6. washthe residue on the filter paper was washed with ethyl acetate
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5dd54b425958405cad3c1974cebe6b3d
Source dataset
uspto-grants-2011_11
Patent number
US08067453B2

Reaction notes

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