Diethyl Oxalate → HCID 359722, compound

HRID 1437615Notes

Reaction equation

HRID 1437615 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH2:6][C:7]#[N:8])=[CH:4][CH:3]=1.[C:11](OCC)(=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13].[H-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([CH:6]([C:7]#[N:8])[C:11](=[O:17])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7268Diethyl OxalateHCID 24758Sodium hydrideHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 359722HCID 359722, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
37.5 °C

Procedure

About 20% of a solution of p-chlorobenzyl cyanide (0.75 g, 4.94 mmol) and diethyl oxalate (0.87 mL, 6.4 mmol) in tetrahydrofuran (one mL) was added to a stirred suspension of sodium hydride (167 mg, 6.95 mmol) in tetrahydrofuran (4 mL). The mixture was heated at 35-40° C. until H2 evolution began. The remaining mixture was added dropwise over about ten minutes. After H2 evolution ceased, part of the solvent was removed under reduced pressure. The residue was diluted with 10 mL of water, neutralized with dilute sulfuric acid and extracted twice with ethyl acetate. The extract was water washed, dried (MgSO4) and stripped to a light brown solid. This was triturated with hexane, filtered and dried to give 1.17 g, (94% yield) of ethyl 3-(4-chlorophenyl)-3-cyano-2-oxopropanoate.

Workup

  1. additionThe remaining mixture was added dropwise over about ten minutes
  2. custompart of the solvent was removed under reduced pressure
  3. additionThe residue was diluted with 10 mL of water
  4. extractionextracted twice with ethyl acetate
  5. washwashed
  6. dry with materialdried (MgSO4)
  7. customThis was triturated with hexane
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-a98fdb6960f641cf8096df4b66978b1f
Source dataset
uspto-grants-2009_11
Patent number
US07622504B2

Reaction notes

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