Tetrahydrofuran → HCID 18707303, compound

HRID 1421971Notes

Reaction equation

HRID 1421971 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].C[N+]1([O-])CC[O:36]CC1.[O:40]1C[CH2:43][CH2:42][CH2:41]1>CO.[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]([CH2:43][CH:42]([OH:36])[CH2:41][OH:40])[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

6

Reactant 3

HCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 70110358HCID 70110358, compound

Product 1

HCID 18707303HCID 18707303, compound

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 887MethanolSolvent

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 of 4-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-0c926fde174e4505aa0d1b7f6ccc5c93
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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