Dimethylformamide → HCID 69203878, compound

HRID 2374469Notes

Reaction equation

HRID 2374469 reaction equation
CS([O:5][CH2:6][CH2:7][CH2:8][C:9]1[O:13][C:12]([N:14]2[CH:18]=[CH:17][N:16]=[C:15]2[CH3:19])=[N:11][C:10]=1[C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)(=O)=O.O[C:28]1[CH:37]=[CH:36][C:31]([C:32](OC)=[O:33])=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([C:10]2[N:11]=[C:12]([N:14]3[CH:18]=[CH:17][N:16]=[C:15]3[CH3:19])[O:13][C:9]=2[CH2:8][CH2:7][CH2:6][O:5][C:28]2[CH:37]=[CH:36][C:31]([CH2:32][OH:33])=[CH:30][CH:29]=2)=[CH:21][CH:22]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7456MethylparabenHCID 11430Potassium CarbonateHCID 18174693HCID 18174693, compound

Product 1

HCID 69203878HCID 69203878, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]propyl methanesulfonate (395 mg), methyl 4-hydroxybenzoate (225 mg), potassium carbonate (276 mg) and N,N-dimethylformamide (10 ml) was stirred at 90° C. for 2 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained yellow oily substance was dissolved in tetrahydrofuran (30 ml), lithium aluminum hydride (80 mg) was added little by little at 0° C., and stirring was carried out at 0° C. for 1 hour. To the reaction mixture, sodium sulfate decahydrate (1.0 g) was added, and stirring was carried out at room temperature for 30 minutes, after which filtration was carried out. The filtrate was concentrated and the residue was purified by silica gel column chromatography. From the fraction eluted with ethyl acetate, 4-({3-[4-(4-chlorophenyl)-2-(2-methyl-1-imidazolyl)-5-oxazolyl]propyl}oxy)benzyl alcohol (304 mg, yield 72%) was obtained as a colorless oily substance.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. dissolutionThe obtained yellow oily substance was dissolved in tetrahydrofuran (30 ml)
  6. additionlithium aluminum hydride (80 mg) was added little by little at 0° C.
  7. stirringstirring
  8. waitwas carried out at 0° C. for 1 hour
  9. additionTo the reaction mixture, sodium sulfate decahydrate (1.0 g) was added
  10. stirringstirring
  11. waitwas carried out at room temperature for 30 minutes
  12. filtrationafter which filtration
  13. concentrationThe filtrate was concentrated
  14. customthe residue was purified by silica gel column chromatography
  15. washFrom the fraction eluted with ethyl acetate

Sources & evidence

ORD record
ord-3edb049b847d43d5bd219c77b6073e6a
Source dataset
uspto-grants-2008_12
Patent number
US07462635B2

Reaction notes

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