Sodium hydride → HCID 14819342, compound

HRID 330273Notes

Reaction equation

HRID 330273 reaction equation
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[Cl:14][C:15]1[C:23]2[O:22][CH2:21][C:20](=O)[C:19]=2[CH:18]=[CH:17][CH:16]=1>C1COCC1>[Cl:14][C:15]1[C:23]2[O:22][CH:21]=[C:20]([CH2:5][C:3]#[N:4])[C:19]=2[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 148193417-Chloro-3(2H)-benzofuranone

Product 1

HCID 14819342HCID 14819342, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of NaH 50% dispersion in mineral oil, washed with hexane; 1.82 g, 0.0378 mol) in THF (70 mL) was added a solution of diethyl cyanomethylphosphonate (6.7 g, 0.0378 mol) in THF (30 mL) dropwise over 20 minutes. After 20 minutes, the mixture was cooled to 0° C. and a solution of 7-chlorobenzofuran-3-one (5.8 g, 0.0344 mol) in THF (80 mL) was added dropwise over 30 minutes. The cooling bath was removed and stirring was continued at room temperature overnight. H2O (400 mL) and ether were added. The organic phase was washed with saturated aqueous NaCl, dried (MgSO4), and concentrated to give a red solid (6.4 g, 97%).

Workup

  1. washwashed with hexane
  2. customThe cooling bath was removed
  3. waitwas continued at room temperature overnight
  4. additionH2O (400 mL) and ether were added
  5. washThe organic phase was washed with saturated aqueous NaCl
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-73e85f9b94f14ff48c00cb054b74ab0b
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

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