Benzene → 1-Cyclopropyl-3-(pyrazin-2-yl)propane-1,3-dione

HRID 1973353Notes

Reaction equation

HRID 1973353 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]([O:9]C)=O.[CH:11]1([C:14]([CH3:16])=[O:15])[CH2:13][CH2:12]1.C[O-].[Na+].C1C=CC=CC=1>O>[CH:11]1([C:14](=[O:15])[CH2:16][C:7]([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][N:1]=2)=[O:9])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 241BenzeneHCID 13004Cyclopropyl methyl ketoneHCID 72662Methyl pyrazinoateHCID 10942334Sodium Methoxide

Product 1

HCID 123605571-Cyclopropyl-3-(pyrazin-2-yl)propane-1,3-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A stirred mixture of 14.0 g. of methyl pyrazinoate, 16.8 g. of cyclopropylmethyl ketone, 6.0 g. of sodium methoxide and 200 ml. of benzene is heated under reflux for 5 hours. A 400 ml. volume of water is added to the mixture. The benzene phase is separated and the aqueous solution is made weakly acidic with dilute hydrochloric acid. A yellow solid precipitates, which is collected and recrystallized from hexane to give white crystals, m.p. 111°-112° C.

Workup

  1. additionA stirred mixture of 14.0 g
  2. temperatureunder reflux for 5 hours
  3. customThe benzene phase is separated
  4. customA yellow solid precipitates
  5. customwhich is collected
  6. customrecrystallized from hexane
  7. customto give white crystals, m.p. 111°-112° C.

Sources & evidence

ORD record
ord-eff6f8eab3f041b68eb3776a0964592a
Source dataset
uspto-grants-1976_12
Patent number
US03997530

Reaction notes

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