Ethane, 2-bromo-1,1-diethoxy- → 2-Phthalimidoacetaldehyde Diethyl Acetal

HRID 451751

Reaktionsgleichung

Reaktionsgleichung von HRID 451751
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].Br[CH2:14][CH:15]([O:19][CH2:20][CH3:21])[O:16][CH2:17][CH3:18]>CN(C=O)C>[CH2:17]([O:16][CH:15]([O:19][CH2:20][CH3:21])[CH2:14][N:5]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6])[CH3:18]

Komponenten

4

Edukt 2

HCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 24194345Phthalimide potassium salt

Produkt 1

HCID 3152862-Phthalimidoacetaldehyde Diethyl AcetalAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A three-necked round-bottomed flask fitted with an efficient stirrer and a reflux condenser was charged with potassium phthalimide (150 g, 0.81 mol) and 2-bromo-1,1-diethoxy-ethane (196 g, 1.0 mol) and DMF (500 mL). The stirrer was started and the mixture was heated for about 3-4 h in an oil bath maintained at 150° C. The solvent DMF was removed under reduced pressure. The residue was purified by column chromatography to afford pure 2-(2,2-diethoxyethyl)isoindoline-1,3-dione (185 g, yield 87%). 1H NMR (400 MHz, MeOD): 1.16 (t, 6H), 3.48-3.60 (m, 2H), 3.68-3.75 (m, 2H), 3.76-3.89 (d, 2H), 4.89 (t, 1H), 7.68-7.75 (m, 2H), 7.85-7.96 (m, 2H). MS (E/Z): 264 (M+H+).

Aufarbeitung

  1. customA three-necked round-bottomed flask fitted with an efficient stirrer and a reflux condenser
  2. temperaturethe mixture was heated for about 3-4 h in an oil bath
  3. customThe solvent DMF was removed under reduced pressure
  4. customThe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-2d6619b0a1ed4a76b51d43a9464d69a5
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487108B2

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