Dicyclohexylcarbodiimide → HCID 54702828, compound

HRID 634840Notes

Reaction equation

HRID 634840 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([OH:11])=O)[O:5][C:6]=1[CH3:7].[OH:12][C:13]1[CH:18]=[C:17]([CH3:19])[O:16][C:15](=[O:20])[CH:14]=1.C1CCC(N=C=NC2CCCCC2)CC1.[Na].C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.CN(C1C=CN=CC=1)C.C(OCC)C>[CH3:1][C:2]1[CH:3]=[C:4]([CH2:8][C:9]([C:14]2[C:15](=[O:20])[O:16][C:17]([CH3:19])=[CH:18][C:13]=2[OH:12])=[O:11])[O:5][C:6]=1[CH3:7]

Participants

9

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 516892Sodium BicarbonateHCID 5360545SodiumHCID 21260728HCID 21260728, compoundHCID 546757574-Hydroxy-6-methyl-2-pyrone

Product 1

HCID 54702828HCID 54702828, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

1.50 g (9.73 mmol) of the 4,5-dimethyl-2-furanacetic acid, 1.22 g (9.67 mmol) of 4-hydroxy-6-methyl-2-pyrone and 2.22 g (10.7 mmol) of DCC were suspended in 30 ml of chloroform, then 244 mg (2.0 mmol) of DMAP added and stirring carried out overnight at 60° C. The reaction liquid was cooled to room temperature and the insoluble material filtered off. The mother liquor was then concentrated and the residue purified by column chromatography. The solid obtained was recrystallized from diethyl ether, and Compound 7 (488 mg, 186 mmol, 19%) obtained. This was converted to the sodium salt with an equivalent quantity of sodium hydrogen carbonate.

Workup

  1. customThe reaction liquid
  2. filtrationthe insoluble material filtered off
  3. concentrationThe mother liquor was then concentrated
  4. customthe residue purified by column chromatography
  5. customThe solid obtained
  6. customobtained

Sources & evidence

ORD record
ord-475d8b680fa145ac813246da4240cf28
Source dataset
uspto-grants-2001_02
Patent number
US06184245B2

Reaction notes

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