Bis(2-chloroethyl) ether → 4-(4-methoxyphenyl)tetrahydro-2H-pyran-4-carbonitrile

HRID 481547Notes

Reaction equation

HRID 481547 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[H-].[Na+].Cl[CH2:15][CH2:16][O:17][CH2:18][CH2:19]Cl>CS(C)=O>[C:10]([C:9]1([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)#[N:11]

Participants

5

Reactant 3

HCID 8115Bis(2-chloroethyl) etherHCID 24758Sodium hydrideHCID 66031Benzeneacetonitrile, 4-methoxy-

Product 1

HCID 9751334-(4-methoxyphenyl)tetrahydro-2H-pyran-4-carbonitrileYield 71%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 4-methoxyphenylacetonitrile (5 g, 34 mmol) and NaH (2.8 g, 71 mmol) in DMSO (50 ml) was added 2-chloroethyl ether (5.3 g, 37 mmol) with cooling. The mixture was stirred at room temperature for 3 h, quenched with water, and extracted with CH2Cl2. The combined extracts were dried (Na2SO4) and concentrated in vacuo to give an oil which was purified by a column chromatography to give Compound 88 (5.3 g, 24 mmol, 71%) as a colorless oil.

Workup

  1. temperaturewith cooling
  2. customquenched with water
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto give an oil which
  7. customwas purified by a column chromatography

Sources & evidence

ORD record
ord-bc2e6fba9f084f9ca13b112099bf69fb
Source dataset
uspto-grants-1998_08
Patent number
US05789423

Reaction notes

Loading…