Ethyl orthoformate → HCID 69743788, compound

HRID 1168132Notes

Reaction equation

HRID 1168132 reaction equation
[CH:1]1([C:4](=[O:26])[CH2:5][C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([CH2:15][N:16]3[C:20](=[O:21])[N:19]([CH:22]4[CH2:24][CH2:23]4)[N:18]=[N:17]3)[C:9]=2[Cl:25])=[O:7])[CH2:3][CH2:2]1.[CH:27](OCC)(OCC)[O:28][CH2:29][CH3:30]>C(OC(=O)C)(=O)C>[CH:1]1([C:4](=[O:26])[C:5](=[CH:27][O:28][CH2:29][CH3:30])[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([CH2:15][N:16]3[C:20](=[O:21])[N:19]([CH:22]4[CH2:24][CH2:23]4)[N:18]=[N:17]3)[C:9]=2[Cl:25])=[O:7])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 12993708HCID 12993708, compound

Product 1

HCID 69743788HCID 69743788, compoundYield 107.1%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

3-Cyclopropyl-1-{3-[(4-cyclopropyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)methyl]-2,4-dichlorophenyl}propan-1,3-dione (2.64 g) was dissolved in acetic anhydride (15 ml) and the solution, after adding triethyl orthoformate (2.12 g), was refluxed for 4 hours upon heating. The solvent was distilled off under reduced pressure and the residue was treated with toluene, which was distilled off under reduced pressure to obtain crude 3-cyclopropyl-1-{3-[(4-cyclopropyl-4,5-dihydro-5-oxo-1H-tetrazol-1-yl)methyl]-2,4-dichlorophenyl}-2-ethoxymethylenepropan-1,3-dione (3.23 g).

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureupon heating
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionthe residue was treated with toluene, which
  5. distillationwas distilled off under reduced pressure

Sources & evidence

ORD record
ord-80354a0957be48c595c47d59fafa31a6
Source dataset
uspto-grants-2003_09
Patent number
US06624121B1

Reaction notes

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