Hydrochloric Acid → 5-[3-[3-methoxy-4-[2-[(E)-styryl]-4-oxazolylmethoxy]phenyl]propyl]-2,4-oxazolidinedione

HRID 1584298ノート

反応式

HRID 1584298 の反応式
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH:13]2[O:17][C:16](=[O:18])[NH:15][C:14]2=[O:19])=[CH:6][C:5]=1[O:20][CH3:21].Cl[CH2:23][C:24]1[N:25]=[C:26](/[CH:29]=[CH:30]/[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:27][CH:28]=1.Cl>CN(C)C=O.O>[CH3:21][O:20][C:5]1[CH:6]=[C:7]([CH2:10][CH2:11][CH2:12][CH:13]2[O:17][C:16](=[O:18])[NH:15][C:14]2=[O:19])[CH:8]=[CH:9][C:4]=1[O:3][CH2:23][C:24]1[N:25]=[C:26](/[CH:29]=[CH:30]/[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[O:27][CH:28]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 220097524-Chloromethyl-2-styryl-oxazoleHCID 698304715-[3-(4-Hydroxy-3-methoxyphenyl)propyl]-2,4-oxazolidinedione

生成物 1

HCID 698307745-[3-[3-methoxy-4-[2-[(E)-styryl]-4-oxazolylmethoxy]phenyl]propyl]-2,4-oxazolidinedione収率 66%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60% in oil, 0.32 g) was added, at 0° C., to a solution of 5-[3-(4-hydroxy-3-methoxyphenyl]propyl]-2,4-oxazolidinedione (1.0 g) in N,N-dimethylformamide (DMF) (20 ml). The mixture was stirred for one hour at room temperature. To the reaction mixture was then added 4-chloromethyl-2-[(E)-styryl]oxazole (0.87 g), which was stirred for 3.5 hours at 90° C. The reaction mixture was poured into water, which was acidified with 2N HCl, followed by extraction with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4) and concentrated under reduced pressure to yield 5-[3-[3-methoxy-4-[2-[(E)-styryl]-4-oxazolylmethoxy]phenyl]propyl]-2,4-oxazolidinedione (1.1 g, 66%). The product was recrystallized from ethyl acetate-hexane to give colorless prisms, m.p.178-179° C.

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-3361ca4e737c4b87b3b68f6119f8dafa
出典データセット
uspto-grants-1999_08
特許番号
US05932601

反応ノート

読み込み中…