Hydrochloric Acid → (5-Cyclopropyl-3-(2,6-dichlorophenyl)isoxazol-4-yl)methanol

HRID 1689802Notes

Reaction equation

HRID 1689802 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.[H-].C([Al+]CC(C)C)C(C)C.Cl>ClCCl>[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 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 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 90.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alternate procedure: Cool a solution of 5-cyclopropyl-3-(2,6-dichloro-phenyl)-isoxazole-4-carboxylic acid methyl ester (62.4 g, 200 mmol) in dichloromethane (400 mL) to 0° C. Add diisobutylaluminum hydride (440 mL, 1.0 M, 440 mmol) while maintaining the temperature between −5° C. and 0° C. Stir the resulting mixture for 30 min. Warm to 15° C. to 25° C. and stir for 3 h. Add the reaction solution to 2.0 M HCl (800 mL) at ˜8° C. to 10° C. Stir for 30 minutes Separate the phases and extract the aqueous phase with dichloromethane (200 mL). Wash the combined organic phases with water (3×100 mL). Concentrate the organic phase to 180 mL total volume. Add heptane (350 mL). Filter the resulting solid to afford 51.5 g (90%) of the title compound.

Workup

  1. temperatureWarm to 15° C. to 25° C.
  2. stirringstir for 3 h
  3. stirringStir for 30 minutes
  4. customSeparate the phases
  5. extractionextract the aqueous phase with dichloromethane (200 mL)
  6. washWash the combined organic phases with water (3×100 mL)
  7. concentrationConcentrate the organic phase to 180 mL total volume
  8. filtrationFilter the resulting solid

Sources & evidence

ORD record
ord-c761aed9ebb44a4483a8f4c7685aab71
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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