Hexane → (4S)-4-propan-2-yl-3-prop-2-enoyl-1,3-oxazolidin-2-one
Reaction equation
[Li]CCCC.CCCCCC.[CH:12]([C@H:15]1[CH2:19][O:18][C:17](=[O:20])[NH:16]1)([CH3:14])[CH3:13].[C:21](Cl)(=[O:24])[CH:22]=[CH2:23].[NH4+].[Cl-]>C1COCC1>[CH:12]([C@H:15]1[CH2:19][O:18][C:17](=[O:20])[N:16]1[C:21](=[O:24])[CH:22]=[CH2:23])([CH3:14])[CH3:13]Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
Production in a way similar to: D. A. Evans, K. T. Chapman, J. Bisha J. Am. Chem. Soc. 1988, 110, 1238; A Studer, T. Hintermann, D. Seebach Helv. Chim. Acta 1995, 78, 1185. 6.88 ml of a 1.6M solution of n-BuLi in hexane (11.0 mmol) is slowly added to a solution of 1.299 g (10.0 mmol) of (S)-4-isopropyl-oxazolidin-2-one in 15 ml of absolute THF at -78° C. The solution is stirred for 30 minutes at -78° C.; 1.22 ml (15.0 mmol) of acrylic acid chloride is added drop by drop; it is allowed to reach room temperature and hydrolyzed with 50 ml of saturated NH4Cl solution. It is extracted three times with 50 ml of Et2O each. After drying on MgSO4, the solvent is removed. By flash-chromatographic purification with pentane/Et2O (10:1), 1.63 g (8.9 mmol, 89%) of 20 is obtained.
Workup
- extractionIt is extracted three times with 50 ml of Et2O each
- customAfter drying on MgSO4
- customthe solvent is removed
- customBy flash-chromatographic purification with pentane/Et2O (10:1)
Sources & evidence
- ORD record
- ord-56cc7c4492014dbdabe389f3f4ebc78a
- Source dataset
- uspto-grants-2000_03
- Patent number
- US06043372
Reaction notes
Loading…