Diazomethane → HCID 72509430, compound

HRID 1825276Notes

Reaction equation

HRID 1825276 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][CH2:11][C:12](Cl)=[O:13])([CH3:3])[CH3:2].[N+:15](=[CH2:17])=[N-:16]>C(Cl)Cl.CCOCC>[N+:15](=[CH:17][C:12](=[O:13])[CH2:11][CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[CH:1]([CH3:3])[CH3:2])=[N-:16]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 22145249HCID 22145249, compound

Product 1

HCID 72509430HCID 72509430, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(2-isopropylphenyl)propanoyl chloride (crude, 10.5 mmole) in methylene chloride was slowly added to a solution of diazomethane (generated from 6.95 g of 1-methyl-3-nitro-1-nitrosoguanidine) in ether (50 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 (20% ethyl acetate/hexanes) to give 1-diazo-4-(2-isopropylphenyl)butan-2-one (1.87 g, 82% over 2 steps) as a bright yellow oil. 1H NMR (CDCl3) δ 7.10-7.30 (4H, m, phenyl), 5.21 (1H, broad s, diazo), 3.15 (1H, m, CH of iPr), 3.00 (2H, t, benzylic), 2.57 (2H, m), 1.24 (6H, d, 2 CH3 of iPr). Step 3:

Workup

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

Sources & evidence

ORD record
ord-2d814a2966614672827094ba0ec247aa
Source dataset
uspto-grants-2006_05
Patent number
US07045591B2

Reaction notes

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