HCID 86666714, compound → HCID 67814280, compound

HRID 2401342Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][O:8][CH2:9][C:10]2[C:14]([C:15]3[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=3[CH:17]=[O:18])=[C:13]([CH3:23])[O:12][N:11]=2)=[CH:5][CH:4]=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([Mg]Br)=[CH:29][CH:28]=1>C1COCC1>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([CH:17]([C:16]2[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=2[C:14]2[C:10]([CH2:9][O:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:25][CH:24]=3)=[N:11][O:12][C:13]=2[CH3:23])[OH:18])=[CH:29][CH:28]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a round bottomed flask was added 2-(3-((4-methoxybenzyloxy)methyl)-5-methylisoxazol-4-yl)benzaldehyde (94 mg, 0.279 mmol) and THF. The solution was cooled to −78° C. before addition of (4-chlorophenyl)magnesium bromide solution (418 μl, 1M in THF, 0.418 mmol) and the reaction stirred at −78° C. for 30 min. The solution was quenched via the addition of water and warmed to room temperature. The aqueous was extracted with EtOAc (3×) and the combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated. The crude residue was purified via Biotage (EtOAc/hex) to afford (4-chlorophenyl)(2-(3-((4-methoxybenzyloxy)methyl)-5-methylisoxazol-4-yl)phenyl)methanol. LC/MS m/z 450 [M+H]+.

Workup

customThe solution was quenched via the addition of water
temperaturewarmed to room temperature
extractionThe aqueous was extracted with EtOAc (3×)
washthe combined organics were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude residue was purified via Biotage (EtOAc/hex)

Sources & evidence

ORD record: ord-b79542bbd14e4112a2ec48f9339aed97
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796261B2

Reaction notes

Loading…