Ethyl orthoformate → HCID 54508074, compound

HRID 266560Notes

Reaction equation

HRID 266560 reaction equation
[CH:1]1([C:4](=[O:18])[CH2:5][C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][C:9]=2[O:16][CH3:17])=[O:7])[CH2:3][CH2:2]1.[CH:19](OCC)(OCC)[O:20][CH2:21][CH3:22]>C(OC(=O)C)(=O)C>[CH:1]1([C:4](=[O:18])[C:5](=[CH:19][O:20][CH2:21][CH3:22])[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14][CH3:15])=[CH:10][C:9]=2[O:16][CH3:17])=[O:7])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 53897219HCID 53897219, compound

Product 1

HCID 54508074HCID 54508074, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 3-cyclopropyl-1-(2-methoxy-4-methylsulphenylphenyl)-propan-1,3-dione (25.4 g) and triethyl orthoformate (39 g) in acetic anhydride was stirred and heated at reflux for 3 hours. After cooling the mixture was evaporated to dryness and the residue was dissolved in toluene and re-evaporated to dryness to give 3-cyclopropyl-2-ethoxymethylene-1-(2-methoxy-4-methylsulphenylphenyl)-propan-1,3-dione (30.6 g) as a red gum which was not further purified.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling the mixture
  4. customwas evaporated to dryness
  5. dissolutionthe residue was dissolved in toluene
  6. customre-evaporated to dryness

Sources & evidence

ORD record
ord-06ce6666a9df47609b3a1ab5201edb53
Source dataset
uspto-grants-1997_07
Patent number
US05650533

Reaction notes

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