Ethanol → HCID 69642321, compound

HRID 1828089Notes

Reaction equation

HRID 1828089 reaction equation
[CH3:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([CH:13]([O:16][Si](C)(C)C)[C:14]#N)[N:3]=1.S(=O)(=O)(O)O.O.C([O-])([O-])=[O:28].[Na+].[Na+].[CH3:33][CH2:34][OH:35]>>[CH2:34]([O:35][C:14](=[O:28])[CH:13]([OH:16])[C:4]1[N:3]=[C:2]([CH3:1])[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=1)[CH3:33]

Participants

6

Reactant 5

HCID 702EthanolHCID 962WaterHCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 22064629HCID 22064629, compound

Product 1

HCID 69642321HCID 69642321, compound

Procedure

To a stirred solution of the crude (RS)-(5-methyl-1-phenyl-1H-[1,2,4]triazol-3-yl)-trimethylsilanyloxy-acetonitrile (2.47 g) in EtOH (20 ml) was added concentrated sulfuric acid (1.73 ml). The mixture was heated to reflux and stirring was continued for 17 h. After cooling to r.t., the mixture (light red clear solution) was poured into 50 ml of water. The solution was brought to pH˜8 by the addition of saturated Na2CO3. It was extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated. The product was isolated by chromatography (silica gel, gradient cyclohexane=>EtOAc) to give (RS)-hydroxy-(5-methyl-1-phenyl-1H-[1,2,4]triazol-3-yl)-acetic acid ethyl ester (1.17 g) as off-white solid. MS 262.2 ([M+H]+)

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. extractionIt was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was isolated by chromatography (silica gel, gradient cyclohexane=>EtOAc)

Sources & evidence

ORD record
ord-0115df9f870e4c66971924a5c33977c4
Source dataset
uspto-grants-2006_06
Patent number
US07056932B2

Reaction notes

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