Triethylamine → 2-[2-[3-Methoxy-4-[(2-phenyl-5-methyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetonitrile

HRID 1294170Notes

Reaction equation

HRID 1294170 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[N:22]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[O:24][C:25]=1[CH3:26])[CH2:6][O:7][C:8]1[C:13]([CH2:14]O)=[CH:12][CH:11]=[CH:10][N:9]=1.[CH2:33]([N:35](CC)CC)C.CS(Cl)(=O)=O.[C-]#N.[Na+]>O.CS(C)=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21]1[N:22]=[C:23]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[O:24][C:25]=1[CH3:26])[CH2:6][O:7][C:8]1[C:13]([CH2:14][C:33]#[N:35])=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8929Sodium CyanideHCID 31297Methanesulfonyl chlorideHCID 68883972[2-[3-Methoxy-4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]methanol

Product 1

HCID 688838762-[2-[3-Methoxy-4-[(2-phenyl-5-methyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetonitrileYield 79%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent3×HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of [2-[-3-methoxy-4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]methanol (540 mg), triethylamine (0.350 mL) and ethyl acetate (50 mL) was dropwise added methanesulfonyl chloride (0.145 mL) under ice-cooling and the mixture was stirred at room temperature for 0.5 hr. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated to give an oil. To a mixture of this oil and dimethyl sulfoxide (10 mL) was added a solution of sodium cyanide (160 mg) in water (1 mL) at room temperature and the mixture was stirred at room temperature for 2 hrs. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The obtained crystals were recrystallized from ethyl acetate-hexane to give crystals (438 mg, 79%) of 2-[2-[3-methoxy-4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetonitrile. melting point: 108-109° C.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customto give an oil
  7. stirringthe mixture was stirred at room temperature for 2 hrs
  8. extractionthe mixture was extracted with ethyl acetate
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated
  12. customThe obtained crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-30fdbff8a4b248b7ad53cfebf006dbdc
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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