Ethyl propiolate → HCID 52044321, compound

HRID 2169059Notes

Reaction equation

HRID 2169059 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[F:10])=[N+:2]=[N-:3].[C:11]([O:15][CH2:16][CH3:17])(=[O:14])[C:12]#[CH:13]>C1(C)C=CC=CC=1>[F:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N:1]1[CH:13]=[C:12]([C:11]([O:15][CH2:16][CH3:17])=[O:14])[N:3]=[N:2]1

Participants

4

Reactant 2

HCID 12182Ethyl propiolateHCID 116079241-Azido-2-fluorobenzene

Product 1

HCID 52044321HCID 52044321, compoundYield 6.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

1-Azido-2-fluorobenzene (1.0 g) and ethyl propiolate (2.2 g) were dissolved in toluene (12 ml) and the mixture was stirred at 100° C. for 13 hr. After cooling to room temperature, the reaction mixture was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (10:90-80:20) was concentrated under reduced pressure to give the object product (111 mg).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. washa fraction eluted with ethyl acetate-hexane (10:90-80:20)
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-05f8315647174d6286b8e942ca77f129
Source dataset
uspto-grants-2015_06
Patent number
US09045436B2

Reaction notes

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