Ethylene Glycol → HCID 54186586, compound

HRID 257500Notes

Reaction equation

HRID 257500 reaction equation
[C:1]1([C:7]2[N:11]([CH2:12][C:13]([OH:15])=[O:14])[N:10]=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(=O)(=O)(O)O.[CH2:21](O)[CH2:22][OH:23]>>[OH:23][CH2:22][CH2:21][O:14][C:13](=[O:15])[CH2:12][N:11]1[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][N:9]=[N:10]1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 1118Sulfuric AcidHCID 6745071H-Tetrazole-1-acetic acid, 5-phenyl-

Product 1

HCID 54186586HCID 54186586, compoundYield 51.8%

Conditions

Temperature
90 °C

Procedure

To a solution of 1 g (4.85 mM) of (5-phenyltetrazol-1-yl) acetic acid in 5 ml of ethylene glycol was added 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 chromatography (eluent: chloroform/methyl alcohol=9/1) for separation and purification, to give 630 mg (yield 51.8%) of (5-phenyltetrazol-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 chromatography (eluent: chloroform/methyl alcohol=9/1) for separation and purification

Sources & evidence

ORD record
ord-098c0f3ff7424774b80cf5aeb8329ef1
Source dataset
uspto-grants-1993_11
Patent number
US05262433

Reaction notes

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