Hydrochloric Acid → HCID 68884132, compound

HRID 1294267Notes

Reaction equation

HRID 1294267 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:31]=[CH:30][C:18]([CH2:19][O:20][C:21]2[CH:22]=[C:23]([CH2:27][C:28]#N)[CH:24]=[N:25][CH:26]=2)=[CH:17][CH:16]=1.O1CCCC1.[OH-:37].[Na+].Cl.[OH2:40]>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:31]=[CH:30][C:18]([CH2:19][O:20][C:21]2[CH:22]=[C:23]([CH2:27][C:28]([OH:40])=[O:37])[CH:24]=[N:25][CH:26]=2)=[CH:17][CH:16]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68883593HCID 68883593, compound

Product 1

HCID 68884132HCID 68884132, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-[5-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetonitrile (0.66 g), tetrahydrofuran (1 mL) and ethanol (5 mL) was added a 2N aqueous sodium hydroxide solution (5 mL) and the mixture was stirred with heating under reflux for 8 hrs. 1N Hydrochloric acid (10 mL) and water were added to the reaction mixture, and the precipitated solid was collected by filtration and dried with air to give crystals (0.67 g, 97%) of 2-[5-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetic acid. Recrystallization from tetrahydrofuran-hexane gave pale-brown prism crystals. melting point: 139-140° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 8 hrs
  3. filtrationthe precipitated solid was collected by filtration
  4. customdried with air

Sources & evidence

ORD record
ord-10ac25f6f5ed4336b2fca2fc0f26ecd7
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

Loading…