Water → HCID 54724707, compound

HRID 1830580Notes

Reaction equation

HRID 1830580 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[C:10]([OH:12])=[O:11].[CH2:13](O)[CH2:14][CH3:15].CCN=C=NCCCN(C)C.O>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1>[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[O:5][C:4](=[O:9])[C:3]=1[C:10]([O:12][CH2:13][CH2:14][CH3:15])=[O:11]

Participants

7

Reactant 4

HCID 962WaterHCID 10311-PropanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 547247064-Hydroxy-6-methyl-2-oxo-2H-pyran-3-carboxylic acid

Product 1

HCID 54724707HCID 54724707, compoundYield 34.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent

Procedure

In 30 ml of toluene, 0.85 g of 4-hydroxy-6-methyl-2-oxo-2H-pyrane-3-carboxylic acid, 0.9 g of 1-propanol and 0.12 g of 4-dimethylaminopyridine were dissolved, and 0.96 g of WSC was added to the mixture, and the mixture was stirred at room temperature for 16 hours. Subsequently, water was poured into the reaction mixture, and the reaction mixture was extracted with ethyl acetate. The resultant organic layer was washed with saturated a saturated solution of sodium chrolide, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to a silica gel column chromatography to obtain 0.37 g of propyl 4-hydroxy-6-methyl-2-oxo-2H-pyrane-3-carboxylate (Compound No. 2).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. washThe resultant organic layer was washed with saturated a saturated solution of sodium chrolide
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-437cabd28a9648fa8a6e612ac734d1c3
Source dataset
uspto-grants-2006_06
Patent number
US07067523B2

Reaction notes

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