Diisobutylaluminum hydride → (5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methanol

HRID 1689759Notes

Reaction equation

HRID 1689759 reaction equation
C[O:2][C:3]([C:5]1[C:6]([C:13]2[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:20])=[N:7][O:8][C:9]=1[CH:10]1[CH2:12][CH2:11]1)=O.CC(C[AlH]CC(C)C)C>C1COCC1.C1(C)C=CC=CC=1>[CH:10]1([C:9]2[O:8][N:7]=[C:6]([C:13]3[C:14]([Cl:20])=[CH:15][CH:16]=[CH:17][C:18]=3[Cl:19])[C:5]=2[CH2:3][OH:2])[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 14487Diisobutylaluminum hydride2×HCID 53421832Methyl 5-cyclopropyl-3-(2,6-dichlorophenyl)-1,2-oxazole-4-carboxylate

Product 1

HCID 45790382(5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methanolYield 93%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

5-Cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazole-4-carboxylic acid methyl ester (0.80 g, 2.6 mmol) is dissolved in 8 mL of THF and is cooled in an ice bath. To the solution is added 1M DIBAL solution in toluene (5.66 mL) and the reaction is stirred one hour. Additional 1M DIBAL solution in toluene (5.66 mL) is added and the reaction is stirred for an additional hour. Upon completion, the reaction is quenched with methanol and acidified with aqueous HCl solution (1M). The reaction mixture is extracted with ethyl acetate and washed with brine. The organic layer is dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield the title compound (0.68 g, 93%). MS m/z: 284.0 (M++1)

Workup

  1. temperatureis cooled in an ice bath
  2. stirringthe reaction is stirred for an additional hour
  3. customUpon completion, the reaction is quenched with methanol
  4. extractionThe reaction mixture is extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6c6601c90ec34feb8867c8e9ad4eeb71
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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