Tetrahydrofuran → HCID 68883980, compound

HRID 1294232Notes

Reaction equation

HRID 1294232 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:53]=[CH:52][C:18]([CH2:19][O:20][C:21]2[CH:22]=[C:23]([CH2:27][C:28]([O:30]CC3C=CC(OCC4N=C(C5C=CC=CC=5)OC=4C)=CC=3)=[O:29])[CH:24]=[CH:25][CH:26]=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:53]=[CH:52][C:18]([CH2:19][O:20][C:21]2[CH:22]=[C:23]([CH2:27][C:28]([OH:30])=[O:29])[CH:24]=[CH:25][CH:26]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68886148HCID 68886148, compound

Product 1

HCID 68883980HCID 68883980, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyl 2-[3-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetate (2.40 g), tetrahydrofuran (7 mL) and ethanol (7 mL) was added 1N aqueous sodium hydroxide solution (7.0 mL) and the mixture was stirred overnight at room temperature. The reaction mixture was concentrated, and water and diethyl ether were added to the residue. Dilute hydrochloric acid was added to acidify the aqueous layer, and the precipitated solid was collected by filtration, and dried with air to give crystals (1.24 g, 85%) of 2-[3-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]phenyl]acetic acid. Recrystallization from acetone-hexane gave colorless prism crystals. melting point: 159-160° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionwater and diethyl ether were added to the residue
  3. additionDilute hydrochloric acid was added
  4. filtrationthe precipitated solid was collected by filtration
  5. customdried with air

Sources & evidence

ORD record
ord-02ebbac50d5f410da743dee75314fa6b
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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