Triethylamine → HCID 68883593, compound

HRID 1294113Notes

Reaction equation

HRID 1294113 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[CH:22]=[C:23]([CH2:27]O)[CH:24]=[N: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[CH:22]=[C:23]([CH2:27][C:31]#[N:33])[CH:24]=[N:25][CH:26]=2)=[CH:29][CH:30]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 8929Sodium CyanideHCID 31297Methanesulfonyl chlorideHCID 68884893HCID 68884893, compound

Product 1

HCID 68883593HCID 68883593, compoundYield 44.2%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of [5-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]methanol (1.68 g), triethylamine (0.85 g) and ethyl acetate (100 mL) was dropwise added methanesulfonyl chloride (0.96 g) at room temperature, and the mixture was stirred at room temperature for 15 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 pale-yellow crystals. To a mixture of the crystals and dimethyl sulfoxide (20 mL) was added an aqueous solution (2 mL) of sodium cyanide (0.41 g) at room temperature and the mixture was stirred at room temperature for 2 days. To the reaction mixture was added water 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 (0.76 g, 44%) of 2-[5-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetonitrile from a fraction eluted with ethyl acetate-hexane (2:1, v/v). Recrystallization from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 137-138° 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 pale-yellow crystals
  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-f99859d066cd439191cebc5959cddc2d
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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