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

HRID 338824

反応式

HRID 338824 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a9fd7562a95a4c17bbc12cb1eea2a2ef
出典データセット
uspto-grants-2014_11
特許番号
US08889704B2

関連ノート

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