Ethyl Acetate → Prop-2-yn-1-yl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate

HRID 602233

Reaktionsgleichung

Reaktionsgleichung von HRID 602233
[CH2:1]([N:3]([CH2:22][CH3:23])[C:4]1[CH:20]=[CH:19][C:7]([C:8]([C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=[O:13])=[O:9])=[C:6]([OH:21])[CH:5]=1)[CH3:2].Cl.CN(C)[CH2:27][CH2:28][CH2:29]N=C=NCC.C(N(C(C)C)C(C)C)C.C(OCC)(=O)C>CN(C=O)C>[CH2:29]([O:13][C:12](=[O:14])[C:11]1[CH:15]=[CH:16][CH:17]=[CH:18][C:10]=1[C:8](=[O:9])[C:7]1[CH:19]=[CH:20][C:4]([N:3]([CH2:1][CH3:2])[CH2:22][CH3:23])=[CH:5][C:6]=1[OH:21])[C:28]#[CH:27]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 798782-[4-(Diethylamino)-2-hydroxybenzoyl]benzoic acidHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Produkt 1

HCID 58675397Prop-2-yn-1-yl 2-[4-(diethylamino)-2-hydroxybenzoyl]benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 200 mmol 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid, 500 mmol propargylic alcohol, 220 mmol 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC), and 500 mmol N-ethyldiisopropylamine in 600 mL DMF is stirred at room temperature for 2 h. 1 L of ethyl acetate is added and the solution extracted with 1 L water. The organic layer is separated, dried (Na2SO4), and the solvent evaporated. The crude product is purified via FC (n-hexane/EtOAC 2:1) yielding 2-(4-diethylamino-2-hydroxybenzoyl)benzoic acid prop-2-ynyl ester. MS (EI): 374 (18%, M+Na+), 352 (100%, M+H+), 296 (17%). UV (EtOH): λmax=356 nm (ε=31'648).

Aufarbeitung

  1. extractionthe solution extracted with 1 L water
  2. customThe organic layer is separated
  3. dry with materialdried (Na2SO4)
  4. customthe solvent evaporated
  5. customThe crude product is purified via FC (n-hexane/EtOAC 2:1)

Quellen und Nachweise

ORD-Eintrag
ord-f5ffeee3a54c4665b59b0d4fa996760b
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906108B2

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