3-Cyano-2-oxotridecanoic acid ethyl ester → 3-Decyl-2,5-Dioxo-4-Hydroxy-3-Pyrroline

HRID 2296343Notes

Reaction equation

HRID 2296343 reaction equation
C([O:3][C:4](=O)[C:5](=[O:19])[CH:6]([C:17]#[N:18])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])C.C([OH:23])C.O>CS(O)(=O)=O>[OH:19][C:5]1[C:4](=[O:3])[NH:18][C:17](=[O:23])[C:6]=1[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 132762403-Cyano-2-oxotridecanoic acid ethyl esterHCID 19096565Water ethanol

Product 1

HCID 546767153-Decyl-2,5-Dioxo-4-Hydroxy-3-Pyrroline

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent

Procedure

1 G. of the 3-cyano-2-oxotridecanoic acid ethyl ester is dissolved in 5 ml of methanesulfonic acid and the mixture allowed to stand overnight at room temperature. The reaction mixture is worked up by first pouring into ethanol-water (20 ml ethanol--5 ml water). After standing for several hours, the ethanol is removed by evaporation. The aqueous acidic residue is diluted further with water and then extracted with chloroform. The chloroform solution is then washed well with water, dried and evaporated to give the desired 3-hydroxy-4-(n-decyl)-3-pyrroline-2,5-dione. Recrystallization from hexane or cyclohexane provides pure 3-hydroxy-4-(n-decyl)-3-pyrroline-2,5-dione, mp 109°-111° C.

Workup

  1. waitAfter standing for several hours
  2. customthe ethanol is removed by evaporation
  3. additionThe aqueous acidic residue is diluted further with water
  4. extractionextracted with chloroform
  5. washThe chloroform solution is then washed well with water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-13c59763b6144e42b025acc7fb2c173c
Source dataset
uspto-grants-1984_01
Patent number
US04428959

Reaction notes

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