Sodium Sulfate → HCID 18707194, compound

HRID 1489263Notes

Reaction equation

HRID 1489263 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([C:19]2[S:20][CH:21]=[C:22]([C:24]3[N:29]=[C:28]([C:30](OCC)=[O:31])[CH:27]=[CH:26][CH:25]=3)[N:23]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH3:18])[CH3:8].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[CH2:7]([O:9][C:10]1[CH:11]=[C:12]([C:19]2[S:20][CH:21]=[C:22]([C:24]3[N:29]=[C:28]([CH2:30][OH:31])[CH:27]=[CH:26][CH:25]=3)[N:23]=2)[CH:13]=[CH:14][C:15]=1[O:16][CH2:17][CH3:18])[CH3:8]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 18707145Ethyl 6-[2-(3,4-diethoxyphenyl)-4-thiazolyl]-2-pyridinecarboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 18707194HCID 18707194, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

200 mg of lithium aluminum hydride was added, at 0° C., to a solution of 1.92 g of 2-(3,4-diethoxyphenyl)-4-(2-ethoxycarbonyl-6-pyridyl)thiazole in 150 ml of tetrahydrofuran. The mixture was stirred in an argon atmosphere for 2 hours. The reaction mixture was mixed with 1 ml of a saturated sodium sulfate slution. The resulting mixture was stirred at 0° C. for 30 minutes and filtered through Celite. The filtrate was concentrated. The residue was purified by silica gel column chromatography and recrystallized from ethyl acetate-n-hexane to obtain 360 mg of 2-(3,4-diethoxyphenyl)-4-(2-hydroxymethyl-6-pyridyl)thiazole.

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for 30 minutes
  2. filtrationfiltered through Celite
  3. concentrationThe filtrate was concentrated
  4. customThe residue was purified by silica gel column chromatography
  5. customrecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-c79b796c29a946d6b39da91bc9b5dbcc
Source dataset
uspto-grants-1997_10
Patent number
US05677319

Reaction notes

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