Ethylene Glycol → HCID 54230610, compound

HRID 257503Notes

Reaction equation

HRID 257503 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C:14]([OH:16])=[O:15])[N:11]=[N:10][N:9]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH2:22](O)[CH2:23][OH:24]>>[OH:24][CH2:23][CH2:22][O:15][C:14](=[O:16])[CH2:13][N:12]1[C:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=2)=[N:9][N:10]=[N:11]1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 1118Sulfuric AcidHCID 972758HCID 972758, compound

Product 1

HCID 54230610HCID 54230610, compoundYield 80.7%

Conditions

Temperature
90 °C

Procedure

To a solution of 300 mg (1.35 mM) of [5-(4-fluorophenyl)tetrazol-1yl] acetic acid in 2 ml of ethylene glycol was added 0.2 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=25/1) for separation and purification, to give 290 mg (yield 80.7%) of [5-(4-fluorophenyl)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 chromatography (eluent: chloroform/methyl alcohol=25/1) for separation and purification

Sources & evidence

ORD record
ord-a8a009c17c3b4e67a94cf449243ec478
Source dataset
uspto-grants-1993_11
Patent number
US05262433

Reaction notes

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