Tetrahydrofuran → 3-[2-[4-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]propenoic acid

HRID 1294348Notes

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:35]=[CH:34][C:18]([CH2:19][O:20][C:21]2[C:26]([CH:27]=[CH:28][C:29]([O:31]CC)=[O:30])=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:17][CH:16]=1.O1CCCC1.[OH-].[Na+]>C(O)C>[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:35]=[CH:34][C:18]([CH2:19][O:20][C:21]2[C:26]([CH:27]=[CH:28][C:29]([OH:31])=[O:30])=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:17][CH:16]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a mixture of ethyl 3-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]propenoate (2.00 g), tetrahydrofuran (10 mL) and ethanol (10 mL) was added a 1N aqueous sodium hydroxide solution (7 mL) and the mixture was stirred at 70° C. for 3 hrs. The reaction mixture was concentrated, and dilute hydrochloric acid was added to acidify the residue. The precipitated solid was collected by filtration and dried with air to give crystals (1.77 g, yield 94%) of 3-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]propenoic acid. Recrystallization from tetrahydrofuran-diisopropyl ether gave colorless prism crystals. melting point: 174-175° C.

Workup

concentrationThe reaction mixture was concentrated
additiondilute hydrochloric acid was added
filtrationThe precipitated solid was collected by filtration
customdried with air

Sources & evidence

ORD record: ord-b606264d2f4f43daa74b61a31ad3f94a
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07238716B2

Reaction notes

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