Triethylamine → HCID 13392138, compound

HRID 1284909Notes

Reaction equation

HRID 1284909 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:15])[NH:10]2.C(N(CC)CC)C.[CH2:23]=[C:24]1[O:28][C:26](=[O:27])[CH2:25]1>C(Cl)(Cl)Cl>[C:26]([O:1][CH2:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:15])[NH:10]2)(=[O:27])[CH2:25][C:24]([CH3:23])=[O:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12661DiketeneHCID 13392135HCID 13392135, compound

Product 1

HCID 13392138HCID 13392138, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2 Grams of 5-(2-hydroxyethoxy)-3,4-dihydrocarbostyril and 2 ml of triethylamine were added to 50 ml of chloroform, then 1 g of diketene was added dropwise thereto, and the whole reaction mixture was stirred at room temperature for 2 days. The insoluble matter formed in the reaction mixture was removed by filtration, and the filtrate was concentrated, then the residue obtained was purified by silica gel column chromatography (eluant: chloroform), the eluate obtained was concentrated and the residue was recrystallized from chloroform-ether to yield 1.5 g of 5-(2-acetoacetoxyethoxy)-3,4-dihydrocarbostyril in the form of colorless needle-like crystals. Melting point: 134.5°-135.5° C.

Workup

  1. customthe whole reaction mixture
  2. customThe insoluble matter formed in the reaction mixture
  3. customwas removed by filtration
  4. concentrationthe filtrate was concentrated
  5. customthe residue obtained
  6. customwas purified by silica gel column chromatography (eluant: chloroform)
  7. customthe eluate obtained
  8. concentrationwas concentrated
  9. customthe residue was recrystallized from chloroform-ether

Sources & evidence

ORD record
ord-8759e4d7da15474bb3c9dc22219ee53a
Source dataset
uspto-grants-1986_01
Patent number
US04564619

Reaction notes

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