Diazomethane → HCID 72509424, compound

HRID 1825273Notes

Reaction equation

HRID 1825273 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][CH2:10][C:11](Cl)=[O:12])[CH3:2].[N+:14](=[CH2:16])=[N-:15]>C(Cl)Cl.CCOCC>[N+:14](=[CH:16][C:11](=[O:12])[CH2:10][CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH2:1][CH3:2])=[N-:15]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 22145275HCID 22145275, compound

Product 1

HCID 72509424HCID 72509424, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(2-ethylphenyl)propanoyl chloride (crude, 23.8 mmole) in methylene chloride was slowly added to a solution of diazomethane (generated from 15.6 g of 1-methyl-3-nitro-1-nitrosoguanidine) in ether (100 ml) cooled in an ice bath. The mixture was then warmed up to room temperature and stirred overnight. The mixture was concentrated in vacuo and purified by column chromatography (10→20% ethyl acetate/hexanes) to give 1-diazo-4-(2-ethylphenyl)butan-2-one (3.47 g, 72% over 2 steps). 1H NMR (CDCl3) δ 7.1-7.25 (4H, m, phenyl), 5.21 (1H, broad s, diazo), 2.97 (2H, m, CH2 of ethyl), 1.20 (3H, t, CH3). Step 3:

Workup

  1. temperaturecooled in an ice bath
  2. concentrationThe mixture was concentrated in vacuo
  3. custompurified by column chromatography (10→20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f62fc180b76a4c81a2034e108bd00655
Source dataset
uspto-grants-2006_05
Patent number
US07045591B2

Reaction notes

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