Ethylene Glycol → HCID 10220346, compound

HRID 257506Notes

Reaction equation

HRID 257506 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[N:10]([CH2:11][C:12]([OH:14])=[O:13])[N:9]=[N:8][N:7]=2)=[CH:2]1.S(=O)(=O)(O)O.[CH2:20](O)[CH2:21][OH:22]>>[OH:22][CH2:21][CH2:20][O:13][C:12](=[O:14])[CH2:11][N:10]1[C:6]([C:3]2[CH:4]=[CH:5][O:1][CH:2]=2)=[N:7][N:8]=[N:9]1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 1118Sulfuric AcidHCID 30775431H-Tetrazole-1-acetic acid, 5-(3-furanyl)-

Product 1

HCID 10220346HCID 10220346, compoundYield 54.6%

Conditions

Temperature
90 °C

Procedure

To a solution of 1 g (5.3 mM) of [5-(3-furyl)tetrazol-1-yl] acetic acid in 5 ml of ethylene glycol was aded 0.5 ml of sulfuric acid. After the addition, the mixture was stirred at 90° C. for 2.5 hrs. The mixture was then poured into ice-water and extracted with ethyl acetate. The organic phase was washed with water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The resultant residue was subjected to silica gel column chromatogrpahy (eluent: chloroform/methyl alcohol=50/1) for separation and purification to give 670 mg (yield 54.6%) of [5-(3-furyl)tetrazol-1-yl] acetic acid 2-hydroxyethyl ester.

Workup

  1. additionAfter the addition
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resultant residue was subjected to silica gel column chromatogrpahy (eluent: chloroform/methyl alcohol=50/1) for separation and purification

Sources & evidence

ORD record
ord-2888ec81d07f4864bcf9f9362f4549b3
Source dataset
uspto-grants-1993_11
Patent number
US05262433

Reaction notes

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