Dimethyl Sulfoxide → (2-Oxopyrrolidin-1-yl)acetaldehyde
Reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][C:15]1=[O:19].CCN(CC)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[O:19]=[C:15]1[CH2:16][CH2:17][CH2:18][N:14]1[CH2:13][CH:12]=[O:11]Participants
7
Conditions
- Temperature
- -78 °C
Procedure
Oxalyl chloride (0.87 mL, 10 mmol) was added dropwise to a solution of DMSO (0.71 mL, 10 mmol) in CH2Cl2 (7 mL) cooled to −78° C. After stirring 15 min at this temperature, 1-(2-hydroxyethyl)-2-pyrrolidinone (1 g, 7.7 mmol) was added dropwise. The mixture was stirred 30 min at −78° C. and Et3N (2.8 mL, 20 mmol) was added dropwise. After allowing the reaction to warm to rt, a solution of NaHCO3 was added and the mixture was extracted with CH2Cl2 (6×). The combined organic layers were dried and concentrated to give the product as an oil: 1H NMR (CDCl3) δ 9.60 (1H, s), 4.16 (2H, s), 3.46 (2H, t, J=7 Hz), 2.45 (2H, t, J=8 Hz), 2.11 (2H, m).
Workup
- additionwas added dropwise
- customthe reaction
- temperatureto warm to rt
- extractionthe mixture was extracted with CH2Cl2 (6×)
- customThe combined organic layers were dried
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-82eb6636c537496d88a372a367818a84
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08691991B2
Reaction notes
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