Tetrahydrofuran → HCID 19603688, compound

HRID 1604693Notes

Reaction equation

HRID 1604693 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[C:22]=4[O:23][CH:24]([CH3:30])[C:25]([O:27]CC)=[O:26])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].O1CCCC1.[OH-].[Na+]>CO>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]4[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[C:22]=4[O:23][CH:24]([CH3:30])[C:25]([OH:27])=[O:26])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 19603838HCID 19603838, compound

Product 1

HCID 19603688HCID 19603688, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-{2-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}-6-methoxyphenoxy}propionate (2.30 g) in a mixed solvent of tetrahydrofuran (30 ml)and methanol (15 ml) was added 1N sodium hydroxide solution (6.8 ml) at room temperature. The solution was stirred for two hours and concentrated under reduced pressure. The residue was diluted with water and acidified with 1N hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with brine and dried over magnesium sulfate to give 2-{2-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yloxy]methyl}-6-methoxyphenoxy}propionic acid (2.17 g) as an amorphous solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-7765fcc4ba1f40a588f4ef0419a9902c
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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