Sodium sulfate decahydrate → HCID 2726773, compound

HRID 1257463Notes

Reaction equation

HRID 1257463 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:26])([F:25])[C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([C:20](OCC)=[O:21])[S:18][CH:19]=2)[CH:12]=[CH:13][CH:14]=1.O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[F:26][C:8]([F:7])([F:25])[C:9]1[CH:10]=[C:11]([C:15]2[N:16]=[C:17]([CH2:20][OH:21])[S:18][CH:19]=2)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 10424923Ethyl 4-[3-(trifluoromethyl)phenyl]-1,3-thiazole-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 2726773HCID 2726773, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere at 0° C., to a solution (50 mL) of lithium aluminum hydride (710 mg, 19 mmol) in tetrahydrofuran was added dropwise a solution (40 mL) of the compound (5.6 g, 19 mmol) obtained in Example 190a in tetrahydrofuran, and the mixture was stirred at 0° C. for 3 hr. After confirmation of the termination of the reaction by TLC, sodium sulfate 10 hydrate was added to the reaction mixture, and the mixture was stirred at room temperature overnight. The resulting salt was removed and the solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (hexane-hexane/ethyl acetate=70/30) to give the title compound (1.2 g, 25%) as an orange oil.

Workup

  1. additionwas added to the reaction mixture
  2. stirringthe mixture was stirred at room temperature overnight
  3. customThe resulting salt was removed
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained crude product
  6. customwas purified by column chromatography (hexane-hexane/ethyl acetate=70/30)

Sources & evidence

ORD record
ord-11567c222f49457482b0d3a918cf7e3f
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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