Pentanal → HCID 67447069, compound

HRID 1022845Notes

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:26]([Li])([CH3:29])([CH3:28])[CH3:27].[Mg+2].[Br-].[Br-].[CH:34](=[O:39])CCCC.[NH4+].[Cl-]>CCOCC.CCCCC>[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]([CH:34]([OH:39])[CH2:27][CH:26]([CH3:29])[CH3:28])=[C:3]([CH3:25])[CH:4]=3)[CH2:12]2)[CH:22]=[C:21]([Cl:23])[CH:20]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 3-(4-bromo-3-methyl-phenyl)-5-(3,5-dichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazole (500 mg) in ether (20 mL) was added tert-butyllithium (1.5 mL of a 1.6 M solution in pentane) at −78° C. After 10 min at this temperature, MgBr2 (0.15 M in THF, 10.3 mL) was added dropwise and left for another 15 min. Valeraldehyde (141 μL, 114 mg) was added and the mixture was stirred at −78° C. for 1 h before it was allowed to warm to room temperature over night. Saturated aqueous NH4Cl solution was added and the mixture was extracted with MTBE. The organic layer was separated, dried (Na2SO4) and concentrated in vacuum. The residue was purified by flash chromatography on silica gel to yield the title compound (230 mg, 45%).

Workup

temperatureto warm to room temperature over night
extractionthe mixture was extracted with MTBE
customThe organic layer was separated
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuum
customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record: ord-af57652bd6b745969d35c35f61c930da
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08722673B2

Reaction notes

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