p-METHYLACETOPHENONE → HCID 66749100, compound

HRID 1749152Notes

Reaction equation

HRID 1749152 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].[H-].[Na+].[CH3:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](=O)[CH3:22])=[CH:17][CH:16]=1>C1COCC1>[C:15]1([CH3:14])[CH:20]=[CH:19][C:18](/[C:21](/[CH3:22])=[CH:3]/[C:1]#[N:2])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8500p-METHYLACETOPHENONEHCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonate

Product 1

HCID 66749100HCID 66749100, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl cyanomethylphosphonate (13.2 g, 74.6 mmol) in 50 mL of THF was added sodium hydride (60% content, 2.98 g, 74.6 mmol). The mixture was stirred at room temperature for 2 hours. 1-(4-methylphenyl)ethanone (5 g, 37.3 mmol) was added and the mixture was stirred for 2 hours. After evaporation of THF, the residue was taken up in ethyl acetate (50 mL) and quenched with water (50 mL). The organic phase was washed with water (50 mL), dried over Na2SO4 and filtered. The filtrate was concentrated in vacuo, and the residue was used in the next step without further purification. LC-MS: m/z 158 (M+H).

Workup

  1. stirringthe mixture was stirred for 2 hours
  2. customAfter evaporation of THF
  3. customquenched with water (50 mL)
  4. washThe organic phase was washed with water (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated in vacuo
  8. customthe residue was used in the next step without further purification

Sources & evidence

ORD record
ord-f31ec644165d4b1b9e16c10dfda87388
Source dataset
uspto-grants-2015_10
Patent number
US09156788B2

Reaction notes

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