Toluene → HCID 21217007, compound

HRID 1586528Notes

Reaction equation

HRID 1586528 reaction equation
[C:1]([C:6]1[C:7](=O)[C:8]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[C:9]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)([O:3][CH2:4][CH3:5])=[O:2].[CH:31]#[C:32][CH2:33][CH2:34][CH2:35][CH2:36]CC.[C:39]1(C)C=CC=CC=1>>[CH2:31]([C:7]1[C:6]([C:1]([O:3][CH2:4][CH3:5])=[O:2])=[C:10]([C:11]2[CH:12]=[CH:13][C:14]([F:17])=[CH:15][CH:16]=2)[C:9]([C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)=[C:8]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:39]=1)[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

4

Reactant 3

HCID 1140TolueneHCID 123701-OctyneHCID 21217005HCID 21217005, compound

Product 1

HCID 21217007HCID 21217007, compound

Procedure

A 250 mL 3 neck round-bottom flask equipped with a condenser was flushed with nitrogen and then loaded with 2,5-dicarboethoxy-3,4-di(4-fluorophenyl)-cyclopentadienone (10 g, 24.3 mmol) and toluene (35 mL) and stirred for 5 min to give a deep orange solution. 1-Octyne (2.67 g, 24.3 mmol) was then added via a syringe to the solution. The reaction was then heated and refluxed for 3 days. The solvent was removed by rotary evaporation and the orange oily liquid was passed through a silica gel column (chloroform).

Workup

  1. customwas flushed with nitrogen
  2. customto give a deep orange solution
  3. temperatureThe reaction was then heated
  4. temperaturerefluxed for 3 days
  5. customThe solvent was removed by rotary evaporation

Sources & evidence

ORD record
ord-fd4519c08aca4c77a2c357b0f18a2775
Source dataset
uspto-grants-1999_08
Patent number
US05945502

Reaction notes

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