Water → 4-[4-[3-(1-Imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)oxazole

HRID 322394ノート

反応式

HRID 322394 の反応式
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:6][CH:5]=1.Cl[CH2:19][C:20]1[N:21]=[C:22]([C:25]2[S:26][CH:27]=[CH:28][CH:29]=2)[O:23][CH:24]=1.O>CN(C)C=O>[N:13]1([CH2:12][CH2:11][CH2:10][C:7]2[CH:8]=[CH:9][C:4]([O:3][CH2:19][C:20]3[N:21]=[C:22]([C:25]4[S:26][CH:27]=[CH:28][CH:29]=4)[O:23][CH:24]=3)=[CH:5][CH:6]=2)[CH:17]=[CH:16][N:15]=[CH:14]1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 25295314-(Chloromethyl)-2-(thiophen-2-yl)-1,3-oxazoleHCID 220098181-[3-(4-Hydroxyphenyl)propyl]imidazole

生成物 1

HCID 98639314-[4-[3-(1-Imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)oxazole収率 89%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (90 mg) was added to a solution of 1-[3-(4-hydroxyphenyl)propyl]imidazole (405 mg) in N,N-dimethyl formamide at room temperature and stirred for 1.5 hours. 4-Chloromethyl-2-(2-thienyl)oxazole (480 mg) was added, and the resultant was stirred at 90° C. for further 2 hours. The reaction mixture was poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure. The residue was subjected to a silica gel chromatography. From the fraction eluted with ethyl acetate-methanol (50:1, v/v), 4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-(2-thienyl)oxazole (650 mg, 89%) was obtained. Recrystallization from ethyl acetate-hexane gave colorless prisms, mp 84-85° C.

後処理

  1. stirringthe resultant was stirred at 90° C. for further 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure
  6. washFrom the fraction eluted with ethyl acetate-methanol (50:1

出典と根拠

ORDレコード
ord-aaa20e4594354ceca64fd08ab2acc231
出典データセット
uspto-grants-2001_04
特許番号
US06211215B1

反応ノート

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