Ammonium Chloride → 4-Ethynyl-5-methyl-3-phenyl-isoxazole

HRID 1695468Notes

Reaction equation

Br[C:2](Br)=[CH:3][C:4]1[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:6][O:7][C:8]=1[CH3:9].C([Mg]Cl)(C)C.[Cl-].[NH4+]>C1COCC1>[C:3]([C:4]1[C:5]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:6][O:7][C:8]=1[CH3:9])#[CH:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 4-(2,2-dibromo-vinyl)-5-methyl-3-phenyl-isoxazole (1.0 g, 2.92 mmol) in THF (6 mL) was added dropwise isopropylmagnesium chloride solution (2M in THF, 2.92 mL, 5.84 mmol) and the resulting solution stirred under argon for 1 h at 0° C. Saturated aqueous ammonium chloride (15 mL) was added and the resulting mixture extracted with ethyl acetate (3×25 mL). The combined organic layers were then dried over sodium sulfate, filtered and concentrated. Purification by chromatography (silica, heptane) afforded the title compound (486 mg, 91%) which was obtained as a yellow oil. MS: m/e=184.2 [M+H]+.

Workup

extractionthe resulting mixture extracted with ethyl acetate (3×25 mL)
dry with materialThe combined organic layers were then dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customPurification by chromatography (silica, heptane)

Sources & evidence

ORD record: ord-5f9eb07cc4ba48d886afd742c485e422
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163728B2

Reaction notes

Loading…