Hydrochloric Acid → (E)-3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propenoic acid

HRID 350150Notes

Reaction equation

[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:33]=[CH:32][C:18]([CH2:19][N:20]2[CH:24]=[C:23](/[CH:25]=[CH:26]/[C:27]([O:29]CC)=[O:28])[CH:22]=[N:21]2)=[CH:17][CH:16]=1.[OH-].[Na+].C(O)C.Cl>O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:33]=[CH:32][C:18]([CH2:19][N:20]2[CH:24]=[C:23](/[CH:25]=[CH:26]/[C:27]([OH:29])=[O:28])[CH:22]=[N:21]2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of ethyl(E)-3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazole-4-yl]propenoate (887 mg), 1 N aqueous sodium hydroxide solution (4 ml), ethanol (8 ml), and tetrahydrofuran (8 ml) was stirred at 40° C. for 3 hours. After the reaction mixture was acidified with 1 N hydrochloric acid, the obtained crystals were collected by filtration, and (E)-3-[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]propenoic acid (672 mg, yield: 81%) was obtained. This was recrystallized from ethanol. Melting point: 186–187° C.

Workup

filtrationthe obtained crystals were collected by filtration

Sources & evidence

ORD record: ord-88bc325a2a8c464eadcdb25370e2e9c8
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07179823B1

Reaction notes

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