Ethyl Acetoacetate → HCID 59379790, Verbindung

HRID 2202724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2202724
[O:1]=[C:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:10]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])[CH:11]=[CH2:12]>O.C(O)(C)(C)C>[C:2]([C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])([CH2:12][CH2:11][C:10]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:12][CH2:11][C:10]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])(=[O:1])[CH3:9]

Komponenten

5

Edukt 2

HCID 8868Ethyl AcetoacetateHCID 15458tert-Butyl acrylate

Produkt 1

HCID 59379790HCID 59379790, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

To a stirred solution of ethyl 3-oxobutanoate (45 g, 345 mmol) and Triton-B (40%, weight % solution in water, 1.08 mg, 6.90 mmol) in tert-BuOH (54 mL) was added tert-butyl acrylate (100.72 g, 691 mmol) dropwise over a period of 30 min under N2 atmosphere. The solution was stirred at room temperature for 24 h. The reaction mixture was partitioned between water (200 mL) and EtOAc (200 mL). The aqueous layer washed with EtOAc (2×50 mL). The combined organic layers were washed with water (200 mL), brine (200 mL), dried over Na2SO4 and concentrated under reduced pressure to provide compound D28-1 (140 g, quant) as a pale yellow oil. 1H NMR (CDCl3, 400 MHz): δ 4.20 (q, J=7.2 Hz 2H), 2.24-2.09 (m, 8H), 1.58 (s, 3H), 1.43 (s, 18H), 1.31 (t, J=7.2 Hz, 3H).

Aufarbeitung

  1. customThe reaction mixture was partitioned between water (200 mL) and EtOAc (200 mL)
  2. washThe aqueous layer washed with EtOAc (2×50 mL)
  3. washThe combined organic layers were washed with water (200 mL), brine (200 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto provide compound D28-1 (140 g, quant) as a pale yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-9a05089e455946a088cd20f65873efb5
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365522B2

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