HCID 18707311, compound → HCID 18707291, compound

HRID 1699582Notes

Reaction equation

HRID 1699582 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]=[C:22]([CH:24]=[O:25])[C:21]([OH:26])=[C:20]([C:27]([O:29][CH3:30])=[O:28])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].B.[Na]>CO>[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]([CH2:24][OH:25])[C:21]([OH:26])=[C:20]([C:27]([O:29][CH3:30])=[O:28])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

4

Reactant 2

HCID 18707311HCID 18707311, compoundHCID 178418435HCID 178418435, compound2×

Product 1

HCID 18707291HCID 18707291, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 20 ml of methanol was suspended 300 mg of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-hydroxy-5-formylphenyl)thiazole with stirring. Threto was added 26.5 mg of sodium boron hydride at 0° C. The mixture was stirred at room temperature for 1 hour. 26.5 mg of sodium boron hydride was further added, and the resulting mixture was stirred at the same temperature for 1 hour. The solvent was removed from the reaction mixture by distillation. To the residue were added 30 ml of dichloromethane and 15 ml of water, and phase separation was conducted. The organic layer was washed with 10 ml of a saturated aqueous sodium chloride solution, dried and subjected to distillation to remove the solvent to obtain 300 mg of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-hydroxy-5-hydroxymethylphenyl)-thiazole.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. stirringthe resulting mixture was stirred at the same temperature for 1 hour
  3. customThe solvent was removed from the reaction mixture by distillation
  4. additionTo the residue were added
  5. custom30 ml of dichloromethane and 15 ml of water, and phase separation
  6. washThe organic layer was washed with 10 ml of a saturated aqueous sodium chloride solution
  7. customdried
  8. distillationsubjected to distillation
  9. customto remove the solvent

Sources & evidence

ORD record
ord-fa6f05a3cc674ca5837542f89f332607
Source dataset
uspto-grants-2002_02
Patent number
USRE037556E1

Reaction notes

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