Methanol → HCID 57070702, compound

HRID 1358499Notes

Reaction equation

HRID 1358499 reaction equation
C([O:8][C@H:9]([C@H:11]([N:22]1[CH:26]=[N:25][C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N:23]1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=1[Cl:21])[CH3:10])C1C=CC=CC=1.I[Si](C)(C)C.CO>C(Cl)(Cl)Cl>[OH:8][C@H:9]([C@H:11]([N:22]1[CH:26]=[N:25][C:24]([C:27]([O:29][CH2:30][CH3:31])=[O:28])=[N:23]1)[CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[C:15]=1[Cl:21])[CH3:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 57080670HCID 57080670, compound

Product 1

HCID 57070702HCID 57070702, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of ethyl 1-[(2S,3R)-2-(benzyloxy)-5-(2,3-dichlorophenyl)-3-pentyl]-1,2,4-triazole-3-carboxylate (103 mg) and iodotrimethylsilane (0.08 ml) in chloroform (4 ml) was stirred at room temperature for 2 hours. The mixture was poured into cold methanol and the whole was evaporated in vacuo. The residue was taken up in ethyl acetate, washed with water, aqueous sodium bisulfite and sodium bicarbonate, successively, and dried. The residue left after evaporation of solvent was purified by column chromatography on silica gel, eluting with a mixture of dichloromethane and methanol (50:1) to give a gummy oil of ethyl 1-[(2S,3R)-2-hydroxy-5-(2,3-dichlorophenyl)-3-pentyl]-1,2,4-triazole-3-carboxylate (32 mg).

Workup

  1. customthe whole was evaporated in vacuo
  2. washwashed with water, aqueous sodium bisulfite and sodium bicarbonate
  3. customsuccessively, and dried
  4. waitThe residue left
  5. customafter evaporation of solvent
  6. customwas purified by column chromatography on silica gel
  7. washeluting with a mixture of dichloromethane and methanol (50:1)

Sources & evidence

ORD record
ord-4800a99524104833ab2c08a6f69cf6eb
Source dataset
uspto-grants-2003_07
Patent number
US06596738B1

Reaction notes

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