Methane → HCID 21398885, compound

HRID 1439249Notes

Reaction equation

HRID 1439249 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[CH3:5][C:6]1[N:7]=[CH:8][C:9]([C:13](OCC)=[O:14])=[N:10][C:11]=1[CH3:12].[OH2:18].C.[C:20]1([CH3:26])C=CC=CC=1>C(OCC)(=O)C.C(OCC)C>[CH3:5][C:6]1[N:7]=[CH:8][C:9]([C:13](=[O:14])[CH2:3][C:2]([O:18][CH2:20][CH3:26])=[O:1])=[N:10][C:11]=1[CH3:12]

Participants

8

Reactant 5

HCID 297MethaneHCID 962WaterHCID 1140TolueneHCID 2723922Sodium ethoxideHCID 21398890Ethyl 5,6-dimethylpyrazine-2-carboxylate

Product 1

HCID 21398885HCID 21398885, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of dry sodium ethoxide (obtained from sodium; 12.7 g.) in anhydrous toluene (200 cc.) is prepared. This suspension is heated to a temperature of about 80° C. and a solution of ethyl 5,6-dimethylpyrazine-2-carboxylate (63 g.) in anhydrous ethyl acetate (104 g.) is added thereto over the course of 1 hour. After the end of the addition, the reaction mixture is heated under reflux for 4 hours and is then cooled to a temperature of about 20° C. and poured into water (1,600 cc.). An insoluble material is filtered off and the organic phase of the filtrate is separated off by decantation. The insoluble material is washed further with water (4 × 400 cc.) and the aqueous filtrates are subsequently used to extract the initial organic phase. The aqueous extracts are recombined, washed with methylene chloride (400 cc.) and then acidified to pH 4 by adding about 4N hydrochloric acid (72 cc.). An oily product separates out and is extracted with methylene chloride (4 × 400 cc.). The organic phases are combined, dried over sodium sulphate and then evaporated to dryness under reduced pressure. The residue obtained is dissolved in diethyl ether (80 cc.) and the cloudy solution obtained is treated with decolorising charcoal (2 g.), filtered and then evaporated to dryness under reduced pressure. Ethyl 3-(5,6-dimethylpyrazin-2-yl)-3-oxo-propionate (30 g.) is thus obtained in the form of an orange oil.

Workup

  1. customis prepared
  2. customover the course of 1 hour
  3. additionAfter the end of the addition
  4. temperaturethe reaction mixture is heated
  5. temperatureunder reflux for 4 hours
  6. temperatureis then cooled to a temperature of about 20° C.
  7. filtrationAn insoluble material is filtered off
  8. customthe organic phase of the filtrate is separated off by decantation
  9. washThe insoluble material is washed further with water (4 × 400 cc.)
  10. extractionto extract the initial organic phase
  11. washwashed with methylene chloride (400 cc.)
  12. additionby adding about 4N hydrochloric acid (72 cc.)
  13. extractionis extracted with methylene chloride (4 × 400 cc.)
  14. dry with materialdried over sodium sulphate
  15. customevaporated to dryness under reduced pressure
  16. customThe residue obtained
  17. customthe cloudy solution obtained
  18. filtrationfiltered
  19. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-bcd204622006462691f4c7c476d57bd4
Source dataset
uspto-grants-1977_11
Patent number
US04058611

Reaction notes

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