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

HRID 2043610Notes

Reaction equation

HRID 2043610 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-60feb2d41a594317a748e1542e9ba839
Source dataset
uspto-grants-2013_11
Patent number
US08586623B2

Reaction notes

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