Acetoin → HCID 58073946, compound

HRID 1470642Notes

Reaction equation

HRID 1470642 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:12]=[CH:11][C:7]([C:8](O)=[O:9])=[CH:6][CH:5]=1.[OH:14][CH:15]([CH3:19])[C:16](=[O:18])[CH3:17].N1C=CC=CC=1.CCN=C=NCCCN(C)C.Cl.Cl>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH3:19][CH:15]([O:14][C:8](=[O:9])[C:7]1[CH:6]=[CH:5][C:4]([C:3]([O:2][CH3:1])=[O:13])=[CH:12][CH:11]=1)[C:16](=[O:18])[CH3:17]

Participants

8

Reactant 5

HCID 179AcetoinHCID 313Hydrochloric AcidHCID 1049PyridineHCID 15513Monomethyl terephthalateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 58073946HCID 58073946, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of terphthalic acid monomethyl ester (1.0 g, 5 mmol), 3-hydroxy-butane-2-one (0.531 g, 6.8 mmol), 4-dimethylamino pyridine (1.27 g, 10 mmol), pyridine (0.79 g, 10 mmol) and EDCl.HCl (1.6 g, 8 mmol) was stirred in dry DMF (10 mL) over night under nitrogen atmosphere. The reaction mixture was poured into ice cold water and extracted with ethyl acetate (100 mL×2). The combined organic layers were washed with water (50 mL×2) and with brine, then dried over anhydrous sodium sulphate and concentrated. the obtained residue was purified by column chromatography using 3% ethyl acetate in hexane to obtain the title compound.

Workup

  1. additionThe reaction mixture was poured into ice cold water
  2. extractionextracted with ethyl acetate (100 mL×2)
  3. washThe combined organic layers were washed with water (50 mL×2) and with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customthe obtained residue was purified by column chromatography

Sources & evidence

ORD record
ord-d136063d823d4fb09d6b4b6ac5c1a768
Source dataset
uspto-grants-2015_04
Patent number
US09006454B2

Reaction notes

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