Ethyl propiolate → Ethyl 3-[4-(methoxymethoxy)-3-methyl phenyl]-5-isoxazolecarboxylate

HRID 393271Notes

Reaction equation

[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[C:2]#[CH:3].[O-]Cl.[Na+].[CH3:11][O:12][CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([CH:19]=[N:20][OH:21])=[CH:17][C:16]=1[CH3:24]>O.C1COCC1.CCOC(C)=O>[CH3:11][O:12][CH2:13][O:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]2[CH:3]=[C:2]([C:1]([O:5][CH2:6][CH3:7])=[O:4])[O:21][N:20]=2)=[CH:17][C:16]=1[CH3:24]

Participants

Conditions

Temperature: 25 °C

Procedure

Ethyl propiolate (0.60 mL, 5.88 mmol) and 6% W/V NaOCl solution in water (10.8 mL) were added to a solution of 4-(methoxymethoxy)-3-methylbenzaldehyde oxime (570 mg, 2.92 mmol) in THF (12 mL). The reaction mixture was stirred at 25° C. for 2 h then was diluted with EtOAc. The resulting solution was successively washed with aqueous 10% Na2S2O3 solution, water and brine, dried (MgSO4), filtered and concentrated under reduced pressure to yield the title compound (745 mg, 88% yield) as a yellow solid.

Workup

washThe resulting solution was successively washed with aqueous 10% Na2S2O3 solution, water and brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-8852ddcb7b3943ddaf05762f67445646
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06806265B2

Reaction notes

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