Tetrahydrofuran → HCID 68885838, compound

HRID 1294276Notes

Reaction equation

HRID 1294276 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:39]=[CH:38][C:18]([CH2:19][O:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2[CH2:31][CH2:32][C:33]([O:35]CC)=[O:34])=[CH:17][CH:16]=1.O1CCCC1.[OH-].[Na+]>C(O)C>[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:16]=[CH:17][C:18]([CH2:19][O:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]=2[CH2:31][CH2:32][C:33]([OH:35])=[O:34])=[CH:38][CH:39]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 68884568HCID 68884568, compound

Product 1

HCID 68885838HCID 68885838, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of ethyl 3-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-1-naphthyl]propionate (1.16 g), tetrahydrofuran (5 mL) and ethanol (5 mL) was added a 1N aqueous sodium hydroxide solution (5 mL) and the mixture was stirred at room temperature for 2 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 (1.03 g, 94%) of 3-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-1-naphthyl]propionic acid. Recrystallization from acetone-hexane gave colorless prism crystals. melting point: 161-162° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additiondilute hydrochloric acid was added
  3. filtrationThe precipitated solid was collected by filtration
  4. customdried with air

Sources & evidence

ORD record
ord-1683eed2d08e4d82bf416dd58a0676ed
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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