Ethyl orthoformate → HCID 13290538, compound

HRID 1903875Notes

Reaction equation

HRID 1903875 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][C:13]1[CH:26]=[CH:25][C:16]([O:17][CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:15][CH:14]=1.[CH:27](OCC)(OCC)OCC>>[F:9][C:8]([F:11])([F:10])[C:6]1[CH:5]=[CH:4][C:3]2[N:12]([C:13]3[CH:14]=[CH:15][C:16]([O:17][CH:18]([CH3:24])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:25][CH:26]=3)[CH:27]=[N:1][C:2]=2[CH:7]=1

Participants

3

Reactant 2

HCID 31214Ethyl orthoformateHCID 13290537HCID 13290537, compound

Product 1

HCID 13290538HCID 13290538, compound

Procedure

5.3 g of 1C was dissolved in 50 ml of triethyl orthoformate, the solution was refluxed for 1 hour, then concentrated under reduced pressure. The residue, an oil, was chromatographed over silica gel, using as eluent a 2:15:33 v/v/v mixture of tetrahydrofuran, ethyl acetate and hexane (hereinafter, Solvent A), to give 1, as a viscous liquid.

Workup

  1. temperaturethe solution was refluxed for 1 hour
  2. concentrationconcentrated under reduced pressure
  3. customThe residue, an oil, was chromatographed over silica gel
  4. additiona 2:15:33 v/v/v mixture of tetrahydrofuran, ethyl acetate and hexane (hereinafter, Solvent A),
  5. customto give 1

Sources & evidence

ORD record
ord-c25c82fc22db4d4e92c74b1d8909161d
Source dataset
uspto-grants-1984_03
Patent number
US04439226

Reaction notes

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