Dicyclohexylcarbodiimide → HCID 54712370, compound

HRID 1870952Notes

Reaction equation

HRID 1870952 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([OH:13])=O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].C1(N=C=NC2CCCCC2)CCCCC1.[OH:29][C:30]1[CH:35]=[C:34]([CH3:36])[O:33][C:32](=[O:37])[CH:31]=1>CN(C)C1C=CN=CC=1.ClCCCl>[OH:29][C:30]1[CH:35]=[C:34]([CH3:36])[O:33][C:32](=[O:37])[C:31]=1[C:11](=[O:13])[CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 158763-Nitrophenylacetic acidHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54712370HCID 54712370, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalyst2×HCID 111,2-DichloroethaneSolvent

Procedure

3-Nitrophenylacetic acid (7.20 g, 39.6 mmol) and then dicyclohexylcarbodiimide (8.6 g, 42 mmol) were added to a 1,2-dichloroethane (100 ml) suspension of 4-hydroxy-6-methyl-2-pyrone (5.00 g, 39.6 mmol) at room temperature, then 4-dimethylaminopyridine (0.24 g, 2.0 mmol) added and stirring carried out for 1 hour at 60° C., after which further 4-dimethylaminopyridine (0.48 g, 4.0 mmol) was added and stirring performed for 6 hours at 60° C. While the solution was still warm, the dicyclohexylurea was filtered off, and the reaction solution washed with dilute hydrochloric acid (50 ml), after which the aqueous layer was extracted with dichloromethane. After drying with anhydrous sodium sulphate, the solvent was distilled off and separation and purification carried out column chromatography. When recrystallization was performed from ethanol, 4-hydroxy-6-methyl-3-(3-nitrophenylacetyl)-2-pyrone (6.60 g, 58%) was obtained as white crystals.

Workup

  1. stirringstirring
  2. waitperformed for 6 hours at 60° C
  3. temperatureWhile the solution was still warm
  4. filtrationthe dicyclohexylurea was filtered off
  5. washthe reaction solution washed with dilute hydrochloric acid (50 ml)
  6. extractionafter which the aqueous layer was extracted with dichloromethane
  7. dry with materialAfter drying with anhydrous sodium sulphate
  8. distillationthe solvent was distilled off
  9. customseparation and purification
  10. customWhen recrystallization

Sources & evidence

ORD record
ord-4e421ddabbce49429d3c388c3f5bed61
Source dataset
uspto-grants-2000_08
Patent number
US06100292

Reaction notes

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