Methanol → HCID 18707240, compound

HRID 1421988Notes

Reaction equation

HRID 1421988 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]([OH:28])C(O)C)[C:21]([O:29][CH2:30]OC)=[C:20]([C:33]([O:35][CH2:36][O:37][CH3:38])=[O:34])[CH:19]=3)[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].I([O-])(=O)(=O)=O.[Na+].[OH2:45].[CH3:46]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]([CH:24]=[O:28])[C:21]([O:29][CH3:30])=[C:20]([C:33]([O:35][CH2:36][O:37][CH3:38])=[O:34])[C:19]=3[O:45][CH3:46])[N:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 4

HCID 887MethanolHCID 962WaterHCID 18707320HCID 18707320, compound2×HCID 23667635Sodium periodate

Product 1

HCID 18707240HCID 18707240, compound

Procedure

In a mixed solvent consisting of 100 ml of tetrahydrofuran and 40 ml of water was dissolved 3.7 g of 2-(3,4-diethoxyphenyl)-4-[3-methoxymethoxycarbonyl-4-methoxymethoxy-5-(1-propenyl)phenyl]thiazole. To the solution were added 100 mg of osmium tetroxide (OsO4) and 5.6 g of sodium periodate (NaIO4), and the mixture was stirred at room temperature for 14 hours. The reaction mixture was filtered. The filtrate was concentrated to a 1/3 volume. To the concentrate was added 100 ml of ethyl acetate, and phase separation was conducted. The organic layer was washed with 40 ml of a saturated aqueous sodium chloride solution, dried and subjected to distillation to remove the solvent. The residue was purified by silica gel column chromatography (elutant: dichloromethane) to obtain 600 mg of 2-(3,4-diethoxyphenyl)-4-(3-methoxymethoxycarbonyl-4-methoxymethoxy-5-formylphenyl)thiazole (compound A) and 1.28 g of 2-(3,4-diethoxyphenyl)-4-[3-methoxymethoxycarbonyl-4-methoxymethoxy-5-(1,2-dihydroxypropyl)phenyl]thiazole (compound B). The 2-(3,4-diethoxyphenyl)-4-[3-methoxymethoxycarbonyl-4-methoxymethoxy-5-(1,2-dihydroxypropyl)phenyl]thiazole (compound B) was dissolved in 40 ml of methanol. To the solution were added 5 g of sodium periodate (NaIO4) and 10 ml of water, and the mixture was stirred at room temperature for 14 hours. The solvent was removed from the reaction mixture by distillation. The residue was mixed with 80 ml of ethyl acetate and 40 ml of water, and phase separation was conducted. The organic layer was washed with 20 ml of a saturated aqueous sodium chloride solution, dried and subjected to distillation to remove the solvent. The residue was combined with 600 mg of the above-obtained 2-(3,4-diethoxyphenyl)-4-(3-methoxymethoxycarbonyl-4-methoxymethoxy-5-formylphenyl)thiazole (compound A). The mixture was recrystallized from ethanol to obtain 1.6 g of 2-(3,4-diethoxyphenyl)-4-(3-methoxymethoxycarbonyl-4-methoxy-methoxy-5-formylphenyl)thiazole as white acicular crystals.

Workup

  1. customThe solvent was removed from the reaction mixture by distillation
  2. additionThe residue was mixed with 80 ml of ethyl acetate and 40 ml of water, and phase separation
  3. washThe organic layer was washed with 20 ml of a saturated aqueous sodium chloride solution
  4. customdried
  5. distillationsubjected to distillation
  6. customto remove the solvent
  7. customThe mixture was recrystallized from ethanol

Sources & evidence

ORD record
ord-496eeed77c274cf09d4baa596bf7711b
Source dataset
uspto-grants-2000_06
Patent number
US06080764

Reaction notes

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