Ammonium Chloride → HCID 22675181, compound

HRID 1005933Notes

Reaction equation

HRID 1005933 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[O:15][C:16]([CH:30]([CH3:32])[CH3:31])=[C:17]([CH2:19][CH2:20][C:21]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)=[O:22])[N:18]=1.[Cl-].[NH4+]>C1COCC1>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[O:15][C:16]([CH:30]([CH3:32])[CH3:31])=[C:17]([CH2:19][CH2:20][CH:21]([C:23]2[CH:24]=[CH:25][C:26]([OH:29])=[CH:27][CH:28]=2)[OH:22])[N:18]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 22675180HCID 22675180, compound

Product 1

HCID 22675181HCID 22675181, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (25 mg, 0.659 mmol) was suspended in THF (5 mL). To the suspension was added 4-[3-[2-(2-chlorophenyl)-5-isopropyl-4-oxazolyl]propionyl]-phenol (240 mg, 0.65 mmol) for 3 minutes under chilling with ice. The mixture was stirred for one hour under cooling with ice, and further stirred for one hour at room temperature. To this was added saturated aqueous ammonium chloride solution under cooling with ice. The mixture was then filtered over celite. After addition of water and ethyl acetate, the organic layer was collected, washed with water, dried over anhydrous sodium sulfate, and filtered. The ethyl acetate was distilled off under reduced pressure, to give 220 mg of the desired compound as pale yellow oil residue (yield 91%).

Workup

  1. temperatureunder chilling with ice
  2. temperatureunder cooling with ice
  3. stirringfurther stirred for one hour at room temperature
  4. temperatureunder cooling with ice
  5. filtrationThe mixture was then filtered over celite
  6. additionAfter addition of water and ethyl acetate
  7. customthe organic layer was collected
  8. washwashed with water
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. distillationThe ethyl acetate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-45e17a3f78d84bc398fca53435529d8d
Source dataset
uspto-grants-2004_09
Patent number
US06787552B2

Reaction notes

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