1-Tridecene, 1-nitro- → Sodium

HRID 1380703Notes

Reaction equation

HRID 1380703 reaction equation
[C:1]([O:11][CH2:12][CH3:13])(=[O:10])[CH2:2][C:3]([C:5]([O:7]CC)=O)=[O:4].[Na:14].[N+:15]([CH:18]=[CH:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])([O-:17])=[O:16]>O1CCCC1.C(Cl)Cl>[C:1]([CH:2]1[CH:19]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:18]([N+:15]([O-:17])=[O:16])[C:5](=[O:7])[C:3]1=[O:4])([O:11][CH2:12][CH3:13])=[O:10].[Na:14]

Participants

6

Reactant 2

HCID 1168981-Tridecene, 1-nitro-HCID 57351814Diethyl 2-oxosuccinate,sodium salt

Product 2

HCID 5360545SodiumHCID 23325904HCID 23325904, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

A suspension of 90% sodium diethyl oxalacetate (17.77 g., 76.1 mmol) in tetrahydrofuran (75 ml) was treated dropwise over a 15 minute period with a solution of 1-nitro-1-tridecene (17.30 g., 76.1 mmol) in methylene chloride (about 100 ml). After a complete solution was obtained the reaction mixture was heated in an 80°-90° C. oil bath and the solvent allowed to distill through a 10 cm vigreux column until the boiling point of the distillate reached 63° C. (100-120 ml of the solvent had distilled). Heating at reflux was continued, with no further distillations, for four hours and 150 ml of distilled water were added over a 5 minute period. The reaction mixture was allowed to cool to 30° C. and then cooled in an ice bath to 10° C. A precipitate began to form when the internal temperature reached about 35° C. and the mixture was stirred for one hour at 10° C. before the precipitate was collected by filtration. The solid was washed three times with 100 ml of isopropanol and then dried under vacuum over phosphorous pentoxide. About 23 g. of 3-carbethoxy-5-nitro-4-undecyl-1,2-cyclopentanedione, sodium salt, m.p. 166°-169° C. (dec) were obtained.

Workup

  1. customAfter a complete solution was obtained the reaction mixture
  2. temperaturewas heated in an 80°-90° C. oil bath
  3. distillationto distill through a 10 cm vigreux column until the boiling point of the distillate
  4. customreached 63° C.
  5. distillation(100-120 ml of the solvent had distilled)
  6. temperatureHeating
  7. temperatureat reflux
  8. addition150 ml of distilled water were added over a 5 minute period
  9. temperaturecooled in an ice bath to 10° C
  10. customto form when the internal temperature
  11. customreached about 35° C.
  12. filtrationwas collected by filtration
  13. washThe solid was washed three times with 100 ml of isopropanol
  14. dry with materialdried under vacuum over phosphorous pentoxide

Sources & evidence

ORD record
ord-bd71a4e70e40403fae95224e3c0887a0
Source dataset
uspto-grants-1986_04
Patent number
US04582940

Reaction notes

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