Diazomethane → Methyl 3-hydroxy-5-hydroxyimino-2-styrylcyclopent-1-eneheptanoate

HRID 1576413ノート

反応式

HRID 1576413 の反応式
[OH:1][CH:2]1[CH2:6][C:5](=[N:7][OH:8])[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[C:3]1[CH:18]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[N+](=[CH2:28])=[N-].N(CNC(N)=O)=O.[OH-].[K+]>C(O)(=O)C.O.C(COC)OC>[OH:1][CH:2]1[CH2:6][C:5](=[N:7][OH:8])[C:4]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([O:17][CH3:28])=[O:16])=[C:3]1[CH:18]=[CH:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

8

反応物 4

HCID 9550Diazomethane2 回HCID 14797Potassium HydroxideHCID 104823Urea, (nitrosomethyl)-HCID 737949793-Hydroxy-5-hydroxyimino-2-styrylcyclopent-1-eneheptanoic acid

生成物 1

HCID 86733982Methyl 3-hydroxy-5-hydroxyimino-2-styrylcyclopent-1-eneheptanoate

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A cold solution of 1 part of 3-hydroxy-5-hydroxyimino-2-styrylcyclopent-1-eneheptanoic acid in 42.3 parts of dimethoxyethane is treated with a cold ethereal solution of diazomethane, prepared from 1.2 parts of N-nitrosomethylurea, 1.4 parts of potassium hydroxide and 2.5 parts of water. That mixture is allowed to react for 2 minutes, after which time, the cold excess diazomethane is decomposed by the careful addition of glacial acetic acid. The ethereal solution is washed with dilute aqueous sodium bicarbonate, then with water and dried over anhydrous sodium sulfate. The ether is removed and the crystalline residue is recrystallized from ethyl acetate-hexane to yield colorless crystals of methyl 3-hydroxy-5-hydroxyimino-2-styrylcyclopent-1-eneheptanoate. That compound melts at about 109°-110° and displays, in chloroform, absorption peaks in the infrared spectrum at about 3590 and 1735 reciprocal centimeters. It is further characterized by the following structural formula ##SPC19##

後処理

  1. customto react for 2 minutes
  2. washThe ethereal solution is washed with dilute aqueous sodium bicarbonate
  3. dry with materialwith water and dried over anhydrous sodium sulfate
  4. customThe ether is removed
  5. customthe crystalline residue is recrystallized from ethyl acetate-hexane

出典と根拠

ORDレコード
ord-fe1664e8fefd4f9290bc7fecf905904e
出典データセット
uspto-grants-1976_09
特許番号
US03980700

反応ノート

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