Ethyl orthoformate → HCID 54487700, compound

HRID 343003Notes

Reaction equation

HRID 343003 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][C:10]([CH:12]2[CH2:14][CH2:13]2)=[O:11])=[C:4]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:3]=1.[CH:20](OCC)(OCC)[O:21][CH2:22][CH3:23]>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[C:9](=[CH:20][O:21][CH2:22][CH3:23])[C:10]([CH:12]2[CH2:13][CH2:14]2)=[O:11])=[C:4]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:3]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 545513651-[4-Chloro-2-(methanesulfonyl)phenyl]-3-cyclopropylpropane-1,3-dione

Product 1

HCID 54487700HCID 54487700, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 1-(4-chloro-2-methylsulphonylphenyl)-3-cyclopropylpropan-1,3-dione (7.1 g) and triethyl orthoformate (6.9 g) in acetic anhydride was stirred and heated at reflux for 2 hours. The mixture was evaporated to dryness, toluene was added and the solution was re-evaporated to give 1-(4-chloro-2-methylsulphonylphenyl)-3-cyclopropyl-2-ethoxymethylenepropan-1,3-dione (8.4 g) as a red gum which was not purified further.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. customThe mixture was evaporated to dryness, toluene
  4. additionwas added
  5. customthe solution was re-evaporated

Sources & evidence

ORD record
ord-5232db05cb5c4e05b1525e510ba4383f
Source dataset
uspto-grants-1999_01
Patent number
US05859283

Reaction notes

Loading…