Water → HCID 66670577, compound

HRID 1005935Notes

Reaction equation

HRID 1005935 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH:24]([CH3:26])[CH3:25])=[C:11]([CH2:13][CH2:14][CH:15]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)O)[N:12]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[O:9][C:10]([CH:24]([CH3:26])[CH3:25])=[C:11]([CH2:13][CH:14]=[CH:15][C:17]2[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=2)[N:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 521998p-Toluenesulfonic acid monohydrateHCID 22675181HCID 22675181, compound

Product 1

HCID 66670577HCID 66670577, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4-[3-[2-(2-chlorophenyl)-5-isopropyl-4-oxazolyl]-1-hydroxypropyl]phenol (110 mg, 0.296 mmol) and p-toluene-sulfonic acid monohydrate (17 mg, 0.092 mmol) were refluxed in toluene (2 mL) for 20 hours. After the starting compounds diminished, the reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was collected, washed with water, dried over anhydrous sodium sulfate, and filtered. The ethyl acetate was removed under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1), to give the desired compound (30 mg) as white crystalline product (yield 28%).

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was collected
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe ethyl acetate was removed under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-a78771ff8fa241bb8d16b729fddca891
Source dataset
uspto-grants-2004_09
Patent number
US06787552B2

Reaction notes

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