Ethyl propiolate → HCID 52044321, compound

HRID 1184247Notes

Reaction equation

HRID 1184247 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-a95fdbb0b48b42eabd424a67da56f323
Source dataset
uspto-grants-2014_03
Patent number
US08664380B2

Reaction notes

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