Water → HCID 70544649、化合物

HRID 1759249ノート

反応式

HRID 1759249 の反応式
[H-].[Na+].[OH:3][C:4]1[C:5]([CH2:10][C:11]2[NH:12][CH:13]=[CH:14][N:15]=2)=[N:6][CH:7]=[CH:8][CH:9]=1.Br[CH2:17][C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=1.O>CN(C)C=O.C(OCC)C>[CH2:25]([O:24][C:22]([C:21]1[CH:20]=[CH:19][C:18]([CH2:17][O:3][C:4]2[C:5]([CH2:10][C:11]3[NH:15][CH:14]=[CH:13][N:12]=3)=[N:6][CH:7]=[CH:8][CH:9]=2)=[CH:28][CH:27]=1)=[O:23])[CH3:26]

参加物

7

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 954261Ethyl 4-(bromomethyl)benzoateHCID 70545010HCID 70545010、化合物

生成物 1

HCID 70544649HCID 70544649、化合物収率 42%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

Sodium hydride (1.81 g of 50% dispersion in mineral oil) was added in portions to a stirred solution of 3-hydroxy-2-(1-imidazolylmethyl)pyridine (6.00 g) in dry N,N-dimethylformamide (100 ml) at 0° C. The mixture was stirred for 15 minutes and a solution of ethyl 4-bromomethyl-benzoate (8.34 g) in dry N,N-dimethylformamide (20 ml) was then added over a period of 10 minutes. The mixture was allowed to warm to room temperature, stirred for 4 hours and water (5 ml) was then added. The solution was evaporated and the residue chromatographed on silica gel, eluting with chloroform. The product-containing fractions were combined and evaporated to give an oil which solidified on trituration with diethyl ether. Recrystallization from diethyl ether gave 3-(4-ethoxycarbonylbenzyloxy)-2-(1-imidazolylmethyl)pyridine (4.85 g), m.p. 100°-101° C.

後処理

  1. stirringstirred for 4 hours
  2. customThe solution was evaporated
  3. customthe residue chromatographed on silica gel
  4. washeluting with chloroform
  5. customevaporated
  6. customto give an oil which
  7. customRecrystallization from diethyl ether

出典と根拠

ORDレコード
ord-a41b42966c4f422b88544b910eb4db3b
出典データセット
uspto-grants-1982_07
特許番号
US04339583

反応ノート

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