Methyl vinyl ketone → HCID 70873097, Verbindung

HRID 1844718Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1844718
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:12]=1)[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[CH3:26][C:27](=[O:30])[CH:28]=[CH2:29]>CCO.[Br-].C([N+]1C(C)=C(CCO)SC=1)C>[C:13]([C:11]1[CH:10]=[C:7]([C:8](=[O:9])[CH2:29][CH2:28][C:27](=[O:30])[CH3:26])[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:12]=1)([CH3:16])([CH3:15])[CH3:14]

Komponenten

6

Edukt 3

HCID 6570Methyl vinyl ketoneHCID 81531DiisopropylethylamineHCID 12682533,5-Bis(tert-butyl)benzaldehyde

Produkt 1

HCID 70873097HCID 70873097, VerbindungAusbeute 44,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromideKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
77.5 °C

Versuchsvorschrift

To a solution of 3,5-di-tert-butylbenzaldehyde (10.9 g, 50 mmol) in EtOH (200 mL) was added DIPEA (12.9 g, 100 mmol), but-3-en-2-one (3.5 g, 50 mmol) and 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide (2.5 g, 10 mmol). This mixture was heated to 75-80° C. overnight, evaporated, diluted with water (50 mL) and extracted with EA. The organic layer was washed with brine, dried, concentrated and purified by CC (EA/PE=1/100) to afford compound 5a (6.4 g, 44%) as colorless oil.

Aufarbeitung

  1. customevaporated
  2. additiondiluted with water (50 mL)
  3. extractionextracted with EA
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated
  7. custompurified by CC (EA/PE=1/100)

Quellen und Nachweise

ORD-Eintrag
ord-6abcab52f0874c1fac30f5091aa109f8
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08946446B2

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