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

HRID 250222Notes

Reaction equation

HRID 250222 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

To a 0° C. solution of 5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazole-4-carboxylic acid methyl ester (0.80 g, 2.6 mmol) in THF (8 mL) is added a 1M DIBAL solution in toluene (5.66 mL). The reaction is stirred one hour. An additional 1M DIBAL solution in Toluene (5.66 mL) is added and the reaction is stirred for an additional hour. The reaction is quenched with methanol and is acidified with aqueous HCl solution (1M). The aqueous solution is extracted with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, and filtered. The solvent is removed under reduced pressure to yield the title compound (0.68 g, 93%). ES/MS m/e 284.0 (M+1).

Workup

  1. stirringthe reaction is stirred for an additional hour
  2. customThe reaction is quenched with methanol
  3. extractionThe aqueous solution is extracted with ethyl acetate
  4. washThe organic layer is washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-0fe56a33907240fda7b6055c5eedf1a7
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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