1-Butanol → HCID 67124168, compound

HRID 1022842Notes

Reaction equation

HRID 1022842 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:12][C:11]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=2)=[CH:4][C:3]=1[CH3:25].C(O)C[CH2:28][CH2:29][OH:30].C(OC=C)=C.C1(NC2CCCCC2)CCCCC1.C(O)CCC>[Pd].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(O)(=O)C.C(OCC)(=O)C>[Cl:24][C:19]1[CH:18]=[C:17]([C:11]2([C:13]([F:16])([F:15])[F:14])[O:10][N:9]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([C:29](=[O:30])[CH3:28])=[C:3]([CH3:25])[CH:4]=3)[CH2:12]2)[CH:22]=[C:21]([Cl:23])[CH:20]=1

Participants

9

Reactant 4

HCID 2631-ButanolHCID 7582DicyclohexylamineHCID 22660526HCID 22660526, compoundHCID 231598123-(4-Bromo-3-methylphenyl)-5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole

Product 1

HCID 67124168HCID 67124168, compoundYield 60%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 812191,3-Bis(diphenylphosphino)propaneCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-(4-bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (500 mg), 1,4-butandiol-monovinyl-ether (385 mg), palladium on charcoal (10%, 23 mg), 1,3-bis(diphenylphosphino)propane (9 mg), dicyclohexylamine (259 mg) and n-butanol (3 mL) were refluxed over night. Ethyl acetate (30 mL) and aqueous acetic acid (1 M, 20 mL) were added, and left at room temperature for 1 h. After separation of the layers, the organic layer was washed with HCl (1 M, 10 mL), dried (Na2SO4) and concentrated in vacuum. The residue was purified by flash chromatography on silica gel to yield the title compound (270 mg, 60%).

Workup

  1. temperaturewere refluxed over night
  2. customAfter separation of the layers
  3. washthe organic layer was washed with HCl (1 M, 10 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuum
  6. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-aecc61fcc4724afca3f05c1983d8109f
Source dataset
uspto-grants-2014_05
Patent number
US08722673B2

Reaction notes

Loading…