HCID 18707380, compound → HCID 18707203, compound

HRID 1489256Notes

Reaction equation

HRID 1489256 reaction equation
B.[Na].[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:25]=[C:24]([CH2:26][CH:27]=[O:28])[C:23]([OH:29])=[C:22]([C:30]([O:32][CH3:33])=[O:31])[CH:21]=3)[N:19]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[CH3:4]>CO>[CH2:3]([O:5][C:6]1[CH:7]=[C:8]([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:25]=[C:24]([CH2:26][CH2:27][OH:28])[C:23]([OH:29])=[C:22]([C:30]([O:32][CH3:33])=[O:31])[CH:21]=3)[N:19]=2)[CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH3:14])[CH3:4]

Participants

4

Reactant 2

HCID 18707380HCID 18707380, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 18707203HCID 18707203, compoundYield 43.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

111 mg of sodium boron hydride was added to a solution of 1.3 g of 2-(3,4-diethoxyphenyl)-4-(3-methoxycarbonyl-4-hydroxy-5-formylmethylphenyl)thiazole in 30 ml of methanol, with stirring under ice-cooling. The mixture was stirred at the same temperature for 30 minutes. After the completion of a reaction, the solvent was removed by distillation. The residue was purified by silica gel column chromatography (eluent: dichloromethane/n-hexane=4/1) and recrystallized from diethyl ether to obtain 570 mg of 2-(3,4-diethoxyphenyl)-4-[3-methoxycarbonyl-4-hydroxy-5-(2-hydroxyethyl)phenyl]-thiazole.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 30 minutes
  3. customAfter the completion of a reaction
  4. customthe solvent was removed by distillation
  5. customThe residue was purified by silica gel column chromatography (eluent: dichloromethane/n-hexane=4/1)
  6. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-5be3bb3e524e431ebb07740b32914180
Source dataset
uspto-grants-1997_10
Patent number
US05677319

Reaction notes

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