Diethyl Ether → HCID 67099355, compound

HRID 1868824Notes

Reaction equation

HRID 1868824 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.Cl[CH2:12][CH2:13][CH2:14][O:15][CH2:16]Cl.C(OCC)C.[H-].[Na+].CN1CCCC1=O>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:9]#[N:10])[CH2:12][CH2:13][CH2:14][O:15][CH2:16]2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydrideHCID 2415824-Chlorobenzyl cyanideHCID 532298903970-18-1

Product 1

HCID 67099355HCID 67099355, compound

Procedure

A mixture of 2-(4-chlorophenyl)acetonitrile (73 g, 483 mmol) and 1-chloro-3-(chloromethoxy)propane (69.1 g, 483 mmol) in ethoxyethane (242 mL, 483 mmol) was added dropwise to a mixture of NaH (57 g, 1437 mmol) in 1-methylpyrrolidin-2-one (1208 mL, 483 mmol) at −20° C. The reaction was stirred for 12 hours and then slowly quenched with H2O. The reaction mixture was extracted with ether (5×), and the combined organic layers were washed with H2O (3×) and brine (1×), dried over Na2SO4, filtered, and concentrated in vacuo to give the desired nitrile as a yellow oil. MS m/e=223.2 (M+H)+.

Workup

  1. customslowly quenched with H2O
  2. extractionThe reaction mixture was extracted with ether (5×)
  3. washthe combined organic layers were washed with H2O (3×) and brine (1×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-445f72e40a674b489fdc8eb40833e01d
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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