Sulfuric Acid → 2-Chloro-3-(2-oxopyrrolidin-1-yl)propanal

HRID 1896387

Reaktionsgleichung

Reaktionsgleichung von HRID 1896387
O[CH2:2][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8].S(=O)(=O)(O)O.[Cl:14][CH:15]=[CH:16]Cl.C([O-])([O-])=[O:19].[K+].[K+]>O>[Cl:14][CH:15]([CH2:2][N:3]1[CH2:7][CH2:6][CH2:5][C:4]1=[O:8])[CH:16]=[O:19]

Komponenten

6

Edukt 4

HCID 1118Sulfuric AcidHCID 109001,2-DichloroethyleneHCID 11430Potassium CarbonateHCID 849112-Pyrrolidinone, 1-(hydroxymethyl)-

Produkt 1

HCID 536291632-Chloro-3-(2-oxopyrrolidin-1-yl)propanal

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

In a 250 ml, three-necked flask fitted with a magnetic stirrer, 1-(hydroxymethyl)pyrrolidin-2-one x82 (15 g, 0.13 mol) is cooled to −10° C. Cold concentrated sulfuric acid (150 ml) is added dropwise. At this temperature, 1,2-dichloroethene (46.73 g, 0.482 mol) is added while the temperature is kept below 0° C. At the end of the addition the mixture is stirred at 40° C. for 2 h. Water is added and the pH is adjusted with K2CO3. The aqueous phase is extracted with CH2Cl2, the combined organic phases are dried over MgSO4, filtered and concentrated. The crude 2-chloro-3-(2-oxopyrrolidin-1-yl)propanal x83 is used in the next step without any further purification.

Aufarbeitung

  1. customIn a 250 ml, three-necked flask fitted with a magnetic stirrer
  2. customis kept below 0° C
  3. additionAt the end of the addition the mixture
  4. extractionThe aqueous phase is extracted with CH2Cl2
  5. dry with materialthe combined organic phases are dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude 2-chloro-3-(2-oxopyrrolidin-1-yl)propanal x83 is used in the next step without any further purification

Quellen und Nachweise

ORD-Eintrag
ord-bb9515b5a4394681a0b7360f5cfcf5e3
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08518943B2

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