Methanol → 2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]pentanoic Acid

HRID 917568Notes

Reaction equation

HRID 917568 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[O:8][N:7]=[C:6]([C:9]2[CH:10]=[C:11]([CH:22]=[CH:23][CH:24]=2)[O:12][CH:13]([CH2:19][CH2:20][CH3:21])[C:14]([O:16]CC)=[O:15])[N:5]=1.CO>O>[CH3:3][C:4]1[O:8][N:7]=[C:6]([C:9]2[CH:10]=[C:11]([CH:22]=[CH:23][CH:24]=2)[O:12][CH:13]([CH2:19][CH2:20][CH3:21])[C:14]([OH:16])=[O:15])[N:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 12042520Ethyl 2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]pentanoate

Product 1

HCID 111734372-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]pentanoic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.1 I of 1N sodium hydroxide solution are added to a solution of 347 g (1.14 mol) of ethyl 2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]-pentanoate in 1.4 I of methanol, and the mixture is stirred at room temperature for 24 hours. The reaction mixture is diluted with 1 I of water and extracted twice with 1 I of tert-butyl methyl ether each time. The aqueous phase is acidified to a pH of 2 using concentrated hydrochloric acid and extracted twice with 2 I of tert-butyl methyl ether each time. The combined organic phases are evaporated, and the residue is recrystallised from 100 ml of toluene: 2-[3-(5-methyl-1,2,4-oxadiazol-3-yl)phenoxy]pentanoic acid is obtained as colourless crystals of m.p. 98-100°.

Workup

  1. extractionextracted twice with 1 I of tert-butyl methyl ether each time
  2. extractionextracted twice with 2 I of tert-butyl methyl ether each time
  3. customThe combined organic phases are evaporated
  4. customthe residue is recrystallised from 100 ml of toluene

Sources & evidence

ORD record
ord-aa87d3208d42404dbc9f4150db749388
Source dataset
uspto-grants-2007_09
Patent number
US07273867B2

Reaction notes

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