2-Azido-1-phenylethanone → Diazoacetophenone

HRID 1803046Notes

Reaction equation

HRID 1803046 reaction equation
[N:1]([CH2:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6])=[N+:2]=[N-].C1(P(C2C=CC=CC=2)CCC(ON2C(=O)CCC2=O)=O)C=CC=CC=1>C1(C)C=CC=CC=1.C(Cl)Cl>[N+:1](=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:6])=[N-:2]

Participants

5

Reactant 2

HCID 109865532-Azido-1-phenylethanoneHCID 426043111-((3-(Diphenylphosphanyl)propanoyl)oxy)pyrrolidine-2,5-dione

Product 1

HCID 18667DiazoacetophenoneYield 49.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of azide 2i (74 mg, 0.459 mmol) in anhydrous toluene (1.5 mL) was cooled to 0° C. A solution of phosphine 1e (171 mg, 0.482 mmol) in toluene (1.0 mL) was added dropwise. The resulting solution was maintained at 0° C. for 2 h and was then allowed to warm to room temperature. The mixture was then diluted with anhydrous CH2Cl2 (5 mL) and was stirred for an additional 30 min. The solution was then placed directly on a column of silica gel and eluted with 15% EtOAc/hexanes to give diazo-compound 5i as a yellow oil (33 mg, 0.226 mmol, 49% yield).

Workup

  1. temperatureto warm to room temperature
  2. washeluted with 15% EtOAc/hexanes

Sources & evidence

ORD record
ord-4cbd1bcd964b4b61b136b28f00a354bf
Source dataset
uspto-grants-2013_01
Patent number
US08350014B2

Reaction notes

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