Triethylamine → 2-Diazonio-3-oxo-1-[(prop-2-en-1-yl)oxy]but-1-en-1-olate

HRID 1905091Notes

Reaction equation

HRID 1905091 reaction equation
C(N(CC)CC)C.[C:8]([O:14][CH2:15][CH:16]=[CH2:17])(=[O:13])[CH2:9][C:10]([CH3:12])=[O:11].C1(C)C=CC(S([N:27]=[N+:28]=[N-])(=O)=O)=CC=1>C(#N)C>[N+:27](=[C:9]([C:10](=[O:11])[CH3:12])[C:8]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])=[N-:28]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13661p-Toluenesulfonyl azideHCID 70701Allyl acetoacetate

Product 1

HCID 541706512-Diazonio-3-oxo-1-[(prop-2-en-1-yl)oxy]but-1-en-1-olateYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

55.4 ml (0.4 mole - 2 equivalents) of triethylamine were added dropwise to a solution, which had been cooled to 0° C., of 28.43 g (0.2 mole) of allyl acetoacetate and 43.39 g (0.22 mole - 1.1 equivalents) of p-toluenesulphonyl azide in 400 ml of anhydrous acetonitrile. The mixture was stirred at 0° C. for 3.5 h, then 50 g of kieselguhr were added, evaporation in vacuo was carried out and then chromatography on 400 g of silica gel (toluene:ethyl acetate 96:4). 31.9 g (95%) of the title compound were obtained as a pale yellow oil, Rf: 0.36 (toluene:ethyl acetate 9:1).

Workup

  1. addition50 g of kieselguhr were added
  2. customevaporation in vacuo

Sources & evidence

ORD record
ord-e35c4e02eeae45339aeec091f483a180
Source dataset
uspto-grants-1989_06
Patent number
US04841042

Reaction notes

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