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

HRID 338824

반응식

HRID 338824 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-a9fd7562a95a4c17bbc12cb1eea2a2ef
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889704B2

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