Sodium Sulfate → HCID 67418080, compound

HRID 1993813Notes

Reaction equation

HRID 1993813 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[C:15]1[O:16][C:17]([CH:32]([CH3:34])[CH3:33])=[C:18]([CH2:20][CH2:21][C:22]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([CH3:31])[CH:25]=2)=[O:23])[N:19]=1.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[Cl:7][C:8]1[CH:13]=[C:12]([Cl:14])[CH:11]=[CH:10][C:9]=1[C:15]1[O:16][C:17]([CH:32]([CH3:34])[CH3:33])=[C:18]([CH2:20][CH2:21][CH:22]([C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([CH3:31])[CH:25]=2)[OH:23])[N:19]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 12993428HCID 12993428, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 67418080HCID 67418080, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of lithium aluminum hydride (92 mg, 2.42 mmol) in dry THF (20 mL), 3-[2-(2,4-dichlorophenyl)-5-isopropyloxazol-4-yl]-1-(4-hydroxy-3-methylphenyl)propan-1-one (1.01 g, 2.41 mmol) was gradually added while cooling with ice. The mixture was stirred for 1 hour, and further stirred at room temperature. The reaction mixture was again cooled with ice. To the mixture, a saturated aqueous sodium sulfate solution was dropwise added. After insoluble materials were filtered out, the solvent was removed under reduced pressure. The residue was extracted with ethyl acetate, washed with water (15 mL) containing a small amount of a 1M aqueous solution of hydrochloric acid, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain the desired compound (997 mg) as ocher yellow crystal (yield 98%).

Workup

  1. temperaturewhile cooling with ice
  2. stirringfurther stirred at room temperature
  3. temperatureThe reaction mixture was again cooled with ice
  4. filtrationAfter insoluble materials were filtered out
  5. customthe solvent was removed under reduced pressure
  6. extractionThe residue was extracted with ethyl acetate
  7. washwashed with water (15 mL)
  8. additioncontaining a small amount of a 1M aqueous solution of hydrochloric acid
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-21d32eb5edea4d67a69e18537e289f24
Source dataset
uspto-grants-2010_01
Patent number
US07652045B2

Reaction notes

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