2-Azido-1-phenylethanone → Diazoacetophenone

HRID 541010Notes

Reaction equation

HRID 541010 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-eba32a62c9d945f28f85eb12f78448b3
Source dataset
uspto-grants-2014_10
Patent number
US08871916B2

Reaction notes

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