Butyl Chloride → 1-Diazopentan-2-one

HRID 648227

Reaction equation

HRID 648227 reaction equation
[CH3:1][N:2]([N:6]=O)[C:3](N)=[O:4].[N+:8](=[CH2:10])=[N-:9].[CH3:11][CH2:12][O:13][CH2:14][CH3:15].[CH2:16](Cl)[CH2:17][CH2:18]C>>[N+:2](=[CH2:1])=[N-:6].[CH3:11][CH2:12][O:13][CH2:14][CH3:15].[N+:8](=[CH:10][C:3](=[O:4])[CH2:16][CH2:17][CH3:18])=[N-:9]

Participants

5

Reactant 3

HCID 8005Butyl ChlorideHCID 12699N-Methyl-N-nitrosoureaHCID 21186548Diazomethane diethylether

Product 2

HCID 21186548Diazomethane diethyletherHCID 537665711-Diazopentan-2-oneYield 97.8%

Procedure

A 100 ml quantity of diazomethane ether solution (containing 2.8 g of diazomethane) is prepared from 10 g of N-methyl-N-nitrosourea. To the diazomethane ether solution is added dropwise 1.7 g of n-butyl chloride with ice-cooling, and the mixture is thereafter stirred for 30 minutes. Nitrogen gas is passed through the reaction mixture at room temperature to remove the excess of diazomethane therefrom. The ethereal solution is distilled in a vacuum, and the residue is purified by column chromatography (silica gel, developed with chloroform) to give 1.75 g of light yellow oily 1-diazo-2-pentanone (yield 97.8%).

Workup

  1. temperaturecooling
  2. customis passed through the reaction mixture at room temperature
  3. customto remove the excess of diazomethane
  4. distillationThe ethereal solution is distilled in a vacuum
  5. customthe residue is purified by column chromatography (silica gel, developed with chloroform)

Sources & evidence

ORD record
ord-ca904204424848a9bda228488484210c
Source dataset
uspto-grants-1983_10
Patent number
US04411911

Linked notes

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