Triethylamine → HCID 68885068, compound

HRID 1294137Notes

Reaction equation

HRID 1294137 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:30]=[CH:29][C:18]([CH2:19][O:20][C:21]2[C:22]([CH2:27]O)=[N:23][CH:24]=[CH:25][CH:26]=2)=[CH:17][CH:16]=1.[CH2:31]([N:33](CC)CC)C.CS(Cl)(=O)=O.[C-]#N.[Na+]>O.CS(C)=O.C(OCC)(=O)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][O:20][C:21]2[C:22]([CH2:27][C:31]#[N:33])=[N:23][CH:24]=[CH:25][CH:26]=2)=[CH:29][CH:30]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8929Sodium CyanideHCID 31297Methanesulfonyl chlorideHCID 68886285HCID 68886285, compound

Product 1

HCID 68885068HCID 68885068, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of [3-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-2-pyridyl]methanol (0.74 g), triethylamine (0.36 g) and ethyl acetate (50 mL) was dropwise added methanesulfonyl chloride (0.41 g) at room temperature and the mixture was stirred at room temperature for 14 hrs. The reaction mixture was washed successively with water saturated aqueous sodium hydrogencarbonate, 1N hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give a yellow oil. To a mixture of this yellow oil and dimethyl sulfoxide (20 mL) was added an aqueous solution (2 mL) of sodium cyanide (0.18 g) at room temperature and the mixture was stirred at room temperature for 2 days. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (0.60 g, 81%) of 2-[3-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-2-pyridyl]acetonitrile from a fraction eluted with ethyl acetate-hexane (1:1, v/v). Recrystallization from ethyl acetate-hexane gave pale-brown prism crystals. melting point: 138-139° C.

Workup

  1. customat room temperature
  2. washThe reaction mixture was washed successively with water saturated aqueous sodium hydrogencarbonate, 1N hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give a yellow oil
  6. stirringthe mixture was stirred at room temperature for 2 days
  7. extractionthe mixture was extracted with ethyl acetate
  8. washThe organic layer was washed successively with water and saturated brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-40b04b6aee754b03bb35487ae7fd5e56
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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