Hydrochloric Acid → HCID 178418576, compound

HRID 1490000Notes

Reaction equation

HRID 1490000 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-af70bb316ad64a35824fc488ec6748d1
Source dataset
uspto-grants-1997_10
Patent number
US05679801

Reaction notes

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