Beta-Nitrostyrene → Ethyl 2-acetyl-4-nitro-3-phenylbutanoate

HRID 642234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 642234
[N+:1]([CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([O-:3])=[O:2].[Na].[C:13]([O:19][CH2:20][CH3:21])(=[O:18])[CH2:14][C:15]([CH3:17])=[O:16]>CCOCC.CCOC(C)=O>[CH2:20]([O:19][C:13](=[O:18])[CH:14]([C:15](=[O:16])[CH3:17])[CH:5]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:4][N+:1]([O-:3])=[O:2])[CH3:21]

Komponenten

5

Edukt 2

HCID 7626Beta-NitrostyreneHCID 87089461Ethyl acetoacetatesodium salt

Produkt 1

HCID 11323434Ethyl 2-acetyl-4-nitro-3-phenylbutanoateAusbeute 106,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of (2-nitro-vinyl)-benzene (2.135 g, 14.3 mmol) in ether (30 mL) at 0° C. was added ethyl acetoacetate sodium salt (2.29 g, 14.3 mmol) portionwise in half minute; after addition, the mixture was stirred at that temperature for 1 hour; then it was diluted with EtOAc, washed with diluted hydrochloride aqueous solution and saturated sodium chloride aqueous solution respectively, the organic phase was dried over anhydrous sodium sulfate, filtered, concentrated, oil-pumped to dryness to give a brown oil, the crude titled product (4.266 g); 1H NMR (200 MHz, CDCl3): δ (ppm)=7.4-7.2 (m, 5H), 4.73 (d, 1H, J=5.9 Hz), 4.2-3.9 (m, 4H), 2.30 (s, 3H), 1.01 (m, 3H).

Aufarbeitung

  1. additionafter addition
  2. washwashed with diluted hydrochloride aqueous solution and saturated sodium chloride aqueous solution respectively
  3. dry with materialthe organic phase was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customoil-pumped to dryness to give a brown oil

Quellen und Nachweise

ORD-Eintrag
ord-e1e9f56439fd43769bd03faf86755bbd
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07696223B2

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