Ethyl orthoformate → HCID 54220402, compound

HRID 266544Notes

Reaction equation

HRID 266544 reaction equation
[CH:1]1([C:4](=[O:24])[CH2:5][C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[C:10]([O:18][CH2:19][CH2:20][O:21][CH3:22])[C:9]=2[Br:23])=[O:7])[CH2:3][CH2:2]1.[CH2:25]([O:27][CH:28](OCC)OCC)[CH3:26]>C(OC(=O)C)(=O)C>[CH:1]1([C:4](=[O:24])[C:5](=[CH:28][O:27][CH2:25][CH3:26])[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[C:10]([O:18][CH2:19][CH2:20][O:21][CH3:22])[C:9]=2[Br:23])=[O:7])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 53671963HCID 53671963, compound

Product 1

HCID 54220402HCID 54220402, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 3-cyclopropyl-1-[2-bromo-3-(2-methoxyethoxy)-4-methylsulphonylphenyl]propan-1,3-dione (7.5 g) and triethylorthoformate (10.3 g) in acetic anhydride was stirred and heated at reflux for 3 hours. It was evaporated to dryness and the residue was treated with xylene and re-evaporated to give crude 3-cyclopropyl-1-[2-bromo-3-(2-methoxyethoxy)-4-methylsulphonylphenyl]-2-ethoxymethylenepropan-1,3-dione (8.5 g) as a dark brown oil which was not purified further.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. customIt was evaporated to dryness
  4. additionthe residue was treated with xylene
  5. customre-evaporated

Sources & evidence

ORD record
ord-4d6436e38bae4014be91031ea6a63ede
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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