Water → (R)-3-methacryloyl-4-phenyloxazolidin-2-one

HRID 338824

Reaction equation

HRID 338824 reaction equation
[C:1]1([C@@H:7]2[CH2:11][O:10][C:9](=[O:12])[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li]CCCC.[C:18](Cl)(=[O:22])[C:19]([CH3:21])=[CH2:20].O>C1COCC1>[C:18]([N:8]1[C@H:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:11][O:10][C:9]1=[O:12])(=[O:22])[C:19]([CH3:21])=[CH2:20]

Participants

6

Reactant 4

HCID 962WaterHCID 13528Methacryloyl chlorideHCID 730425(4R)-4-phenyl-1,3-oxazolidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 677330(R)-3-methacryloyl-4-phenyloxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of (R)-4-phenyloxazolidin-2-one (65.00 g, 398.3 mmol) in dry THF (612.8 mL) at −78° C. was quickly added n-BuLi (167.3 mL, 418.3 mmol) dropwise, and the mixture was stirred at −78° C. for 0.5 hours. To this cold stirring solution was quickly added dropwise a solution of methacryloyl chloride (40.86 mL, 418.3 mmol) in THF (60 mL), and the mixture was allowed to warm to ambient temperature and stirred for 0.5 hours. Water (300 mL) was added and the suspension was stirred for 1 hour and then filtered to give desired product as a hard solid cake (66 g). The filtrate was concentrated under reduced pressure to a yellow solid residue, which was taken up in Et2O (400 mL) and filtered to give additional pure desired product (9 g). The products were combined to give (R)-3-methacryloyl-4-phenyloxazolidin-2-one (75 g, 81% yield).

Workup

  1. customat −78° C.
  2. temperatureto warm to ambient temperature
  3. stirringstirred for 0.5 hours
  4. stirringthe suspension was stirred for 1 hour
  5. filtrationfiltered

Sources & evidence

ORD record
ord-a9fd7562a95a4c17bbc12cb1eea2a2ef
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Linked notes

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