Hydrochloric Acid → HCID 178418576, compound

HRID 5251

Reaction equation

HRID 5251 reaction equation
[CH2:1]1[C:6](=[O:7])[O:5][CH2:4][C:2]1=[O:3].C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.[CH2:27]([C:34]1[CH:49]=[CH:48][C:37]([O:38][CH:39](C)[CH2:40][CH2:41][CH2:42][CH2:43][C:44](O)=[O:45])=[CH:36][CH:35]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].Cl>CN(C)C=O.CN(C)C1C=CN=CC=1>[CH2:27]([C:34]1[CH:49]=[CH:48][C:37]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][C:44]([C:1]2[C:6](=[O:7])[O:5][CH2:4][C:2]=2[OH:3])=[O:45])=[CH:36][CH:35]=1)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 521261Tetronic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 229027806-(4-Heptylphenoxy)heptanoic acid

Product 1

HCID 178418576HCID 178418576, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 1.1 g (10.98 mmol) of tetronic acid in 25 mL of dimethylformamide is added 1.53 mL (10.98 mmol) of triethylamine and 400 mg of 4-dimethylaminopyridine at 0° C. Next, 2.28 g (11.98 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 3.38 g (10.98 mmol) of 6-(4-heptylphenoxy)heptanoic acid are added and the reaction mixture is stirred for 3 days at room temperature. The reaction mixture is acidified with 1.0N HCl and extracted with three 200 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo. Trituration of the crude product in ethyl acetate/hexane affords 2.1 g (50%) of 3-[6-(4-heptylphenoxy)-1-oxohexyl]-4-hydroxy-2(5H)-furanone.

Workup

  1. extractionextracted with three 200 mL portions of ether
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-97431224e9364eb9a27d4b64804e66df
Source dataset
uspto-grants-1993_09
Patent number
US05242945

Linked notes

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