Sodium hydride → HCID 45381710, compound

HRID 1402883Notes

Reaction equation

HRID 1402883 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=O)=[CH:17][CH:16]=1>COCCOC>[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22]/[C:23](/[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:3]/[C:1]#[N:2])=[CH:19][CH:20]=1.[Cl:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][CH2:22]/[C:23](/[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:3]\[C:1]#[N:2])=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 2447713-(4-chlorophenyl)-1-phenylpropan-1-one

Product 2

HCID 45381710HCID 45381710, compoundHCID 66759042HCID 66759042, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Diethyl cyanomethylphosphonate (0.8 ml) was added dropwise at rt to a slurry of sodium hydride (60% in mineral oil, 0.2 g) in anhydrous 1,2-dimethoxyethane (15 ml) under nitrogen atmosphere. The reaction mixture was stirred at rt for 1 hour and 3-(4-chlorophenyl)-1-phenylpropan-1-one (0.4 g) was added. After stirring at 80° C. for 4 h the resultant solution was poured into ice water (50 ml) and extracted with dichloromethane (3×20 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4), and evaporated in vacuo. The crude mixture was separated by flash chromatography on silica gel (hexane/ethyl acetate 10:1) to afford (Z)-5-(4-chlorophenyl)-3-phenylpent-2-enenitrile (80 mg) and (E)-5-(4-chlorophenyl)-3-phenylpent-2-enenitrile (284 mg) as colourless oils.

Workup

  1. extractionextracted with dichloromethane (3×20 ml)
  2. washThe combined organic layers were washed with brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe crude mixture was separated by flash chromatography on silica gel (hexane/ethyl acetate 10:1)

Sources & evidence

ORD record
ord-43a056641e3e4af3abc405aefba1f619
Source dataset
uspto-grants-2014_12
Patent number
US08912186B2

Reaction notes

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