Diethyl Ether → HCID 67099621, compound

HRID 1868642Notes

Reaction equation

HRID 1868642 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]#[N:12])=[CH:6][CH:5]=1.Cl[CH2:14][O:15][CH2:16][CH2:17]Cl.C(OCC)C>CN1CCCC1=O>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:11]#[N:12])[CH2:17][CH2:16][O:15][CH2:14]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 2415824-Chlorobenzyl cyanideHCID 102908101-Chloro-2-(chloromethoxy)ethane

Product 1

HCID 67099621HCID 67099621, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of the NaH (60% by weight, 4 g, 98 mmol) and 1-methylpyrrolidin-2-one (82.5 mL) at −20° C., was added dropwise a mixture of 2-(4-chlorophenyl)acetonitrile (5 g, 33 mmol) and 2-chloroethyl chloromethyl ether (4 mL, 33 mmol) in diethyl ether (16.5 mL, 33 mmol). The mixture was allowed to warm to room temperature over 24 hours. The reaction was then slowly quenched with ice water and extracted with ether (3×). The organic layers were combined, washed with H2O (3×) and brine, dried over Na2SO4, concentrated in vacuo, and purified by silica flash chromatography (13% EtOAc/hexane) to give the desired compound as a yellow oil. MS m/e=208.0 (M+H)+.

Workup

  1. customThe reaction was then slowly quenched with ice water
  2. extractionextracted with ether (3×)
  3. washwashed with H2O (3×) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by silica flash chromatography (13% EtOAc/hexane)

Sources & evidence

ORD record
ord-5ef5c85b7e754b1eb0a2a8e443d20bcc
Source dataset
uspto-grants-2009_12
Patent number
US07635715B2

Reaction notes

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