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

HRID 1576413Notes

Reaction equation

HRID 1576413 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

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##

Workup

  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

Sources & evidence

ORD record
ord-fe1664e8fefd4f9290bc7fecf905904e
Source dataset
uspto-grants-1976_09
Patent number
US03980700

Reaction notes

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