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

HRID 1294135Notes

Reaction equation

HRID 1294135 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:26]([CH2:27]O)=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:17][CH:16]=1.[CH2:31]([N:33](CC)CC)C.CS(Cl)(=O)=O.[C-]#N.[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.O.C(#N)C.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:26]([CH2:27][C:31]#[N:33])=[CH:25][CH:24]=[CH:23][N:22]=2)=[CH:29][CH:30]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 8929Sodium CyanideHCID 31297Methanesulfonyl chlorideHCID 68884965[2-[4-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]methanol

Product 1

HCID 688841392-[2-[4-[(5-Methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetonitrileYield 36%

Reagents, catalysts & solvents 4

HCID 159952Benzyltributylammonium chlorideCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of [2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]methanol (1.50 g), triethylamine (0.75 g) and ethyl acetate (150 mL) was dropwise added methanesulfonyl chloride (0.85 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 and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give an oil. A mixture of this oil, sodium cyanide (0.72 g), benzyltributylammonium chloride (0.59 g), acetonitrile (20 mL) and water (10 ml) was stirred at room temperature for 15 hrs. The reaction mixture was concentrated, and ethyl acetate was added to the residue. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals (0.55 g, 36%) of 2-[2-[4-[(5-methyl-2-phenyl-4-oxazolyl)methoxy]benzyloxy]-3-pyridyl]acetonitrile from a fraction eluted with ethyl acetate-hexane (1:4, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 149-150° C.

Workup

  1. customat room temperature
  2. washThe reaction mixture was washed successively with water, saturated aqueous sodium hydrogencarbonate and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customto give an oil
  6. stirringwas stirred at room temperature for 15 hrs
  7. concentrationThe reaction mixture was concentrated
  8. additionethyl acetate was added to the residue
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-ba79d4829d6f4fcfa312d99ebf452900
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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