Toluene → HCID 69310607, compound

HRID 750920Notes

Reaction equation

HRID 750920 reaction equation
[C:1]([CH:3]=[C:4]1[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:20][C@@H:19]([CH2:21][N:22]=[N+:23]=[N-:24])[O:18][C:17]3=[O:25])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)#[N:2].[C:26]([O:30]CC)(=[O:29])[C:27]#[CH:28].[C:33]1(C)C=CC=C[CH:34]=1>>[C:1]([CH:3]=[C:4]1[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][C:13]([N:16]3[CH2:20][C@@H:19]([CH2:21][N:22]4[CH:34]=[C:33]([CH2:28][CH2:27][C:26]([OH:30])=[O:29])[N:24]=[N:23]4)[O:18][C:17]3=[O:25])=[CH:12][CH:11]=2)[CH2:8][CH2:9]1)#[N:2]

Participants

4

Reactant 3

HCID 1140TolueneHCID 12182Ethyl propiolateHCID 86591703HCID 86591703, compound

Product 1

HCID 69310607HCID 69310607, compoundYield 70%

Procedure

The mixture of compound of Example 1 (2.05 mmol), ethyl propiolate (4.21 mmol), in toluene (10 ml) was heated under reflux for 4 hours. The solvent was removed under vacuum. The residue was triturated with the hexane and filtered to provide a isomeric mixture of two compounds. The column chromatographic purification on silica gel afforded the titled compound in 70% yield.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe solvent was removed under vacuum
  3. customThe residue was triturated with the hexane
  4. filtrationfiltered
  5. customto provide
  6. additiona isomeric mixture of two compounds
  7. customThe column chromatographic purification on silica gel

Sources & evidence

ORD record
ord-b58e93a91d8148b3bec9f6534229cbd2
Source dataset
uspto-grants-2008_07
Patent number
US07405228B2

Reaction notes

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