HCID 70110358, compound → HCID 18707303, compound

HRID 1699566Notes

Reaction equation

HRID 1699566 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([OH:27])(CC=C)[CH:20]([C:28]([O:30][CH3:31])=[O:29])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]>CO.O1CCCC1.[Os](=O)(=O)(=O)=O>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:13]2[S:14][CH:15]=[C:16]([C:18]3[CH:23]=[C:22]([CH2:5][CH:4]([OH:3])[CH2:9][OH:10])[C:21]([OH:27])=[C:20]([C:28]([O:30][CH3:31])=[O:29])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 1

HCID 70110358HCID 70110358, compound

Product 1

HCID 18707303HCID 18707303, compoundYield 160.4%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1 g of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-hydroxy-4-allylphenyl)thiazole in 20 ml of methanol and 20 ml of tetrahydrofuran were added 0.5 ml of osmium tetroxide (a 4% aqueous solution) and 1.22 g of4-methylmorpholine N-oxide. The mixture was stirred at room temperature for 4 hours. The solvent was removed by distillation. The residue was mixed with 50 ml of dichloromethane and 25 ml of water for phase separation. The organic layer was washed with 25 ml of a saturated aqueous sodium chloride solution and dried. The solvent was removed by distillation. The residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=199/1) to obtain 860 mg of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-hydroxy-5-(2,3-dihydroxypropyl)phenyl]thiazole.

Workup

  1. customThe solvent was removed by distillation
  2. additionThe residue was mixed with 50 ml of dichloromethane and 25 ml of water for phase separation
  3. washThe organic layer was washed with 25 ml of a saturated aqueous sodium chloride solution
  4. customdried
  5. customThe solvent was removed by distillation
  6. customThe residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=199/1)

Sources & evidence

ORD record
ord-8a4b23440ca44ccd9b22f57f0d24c110
Source dataset
uspto-grants-2002_02
Patent number
USRE037556E1

Reaction notes

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