Sodium hydride → HCID 13415097, compound

HRID 880399Notes

Reaction equation

HRID 880399 reaction equation
COP([CH2:7][C:8]([O:10][CH3:11])=[O:9])(OC)=O.[H-].[Na+].[CH:14]([C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[C:19]#[N:20])=O>C1COCC1.CCCCCCC>[C:19]([C:18]1[CH:17]=[C:16](/[CH:14]=[CH:7]/[C:8]([O:10][CH3:11])=[O:9])[CH:23]=[CH:22][CH:21]=1)#[N:20]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 80029Trimethyl phosphonoacetateHCID 90670m-Formylbenzonitrile

Product 1

HCID 13415097HCID 13415097, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8900HeptaneSolvent

Procedure

Methyl 2-(dimethoxyphosphoryl)acetate (20.83 g, 114.39 mmol) was dissolved in THF (500 mL). Sodium hydride (4.58 g, 114.39 mmol) was added in small portions. 3-formylbenzonitrile (10 g, 76.26 mmol) was added dissolved in 50 mL of THF and the reaction mixture was stirred at rt for 2 h. The reaction mixture was diluted with heptane, washed with H2O, dried over sodium sulfate, filtered and concentrated under reduced pressure. The resulting solid was triturated in heptane, filtered, washed with heptane and dried under vacuum, giving 13.26 g title compound (93%) as a white powder. 1H NMR (400 MHz, CDCl3) δ ppm 3.83 (s, 3H) 6.50 (d, J=16.02 Hz, 1H) 7.52 (t, J=7.81 Hz, 1H) 7.61-7.84 (m, 4H).

Workup

  1. washwashed with H2O
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting solid was triturated in heptane
  6. filtrationfiltered
  7. washwashed with heptane
  8. customdried under vacuum

Sources & evidence

ORD record
ord-7047ea68e9694eefba8c8b04f7a7c496
Source dataset
uspto-grants-2015_03
Patent number
US08993577B2

Reaction notes

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