Ethyl orthoformate → HCID 53795986, compound

HRID 1491557Notes

Reaction equation

HRID 1491557 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:5]=[CH:4][C:3]=1[C:13](=[O:20])[CH2:14][C:15]([CH:17]1[CH2:19][CH2:18]1)=[O:16].[CH:21](OCC)(OCC)[O:22][CH2:23][CH3:24]>C(OC(=O)C)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][S:9]([CH3:12])(=[O:10])=[O:11])[CH:5]=[CH:4][C:3]=1[C:13](=[O:20])[C:14](=[CH:21][O:22][CH2:23][CH3:24])[C:15]([CH:17]1[CH2:18][CH2:19]1)=[O:16]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 18953281HCID 18953281, compound

Product 1

HCID 53795986HCID 53795986, compoundYield 102%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 1-[2-chloro-4-(methylsulphonyloxy)phenyl]-3-cyclopropylpropan-1.3-dione (4.75 g) and triethyl orthoformate (4.5 g) in acetic anhydride was stirred and heated at reflux for 3 hours. The mixture was cooled and evaporated to dryness. Toluene was added and the mixture as re-evaporated to give 1-[2-chloro-4-(methylsulphonyloxy)phenyI]-3-cyclopropyl-2-ethoxymethylenepropan-1,3-dione (5.7 g) as a brown oil which was not further purified.

Workup

  1. temperatureheated
  2. temperatureat reflux for 3 hours
  3. temperatureThe mixture was cooled
  4. customevaporated to dryness
  5. additionToluene was added
  6. customthe mixture as re-evaporated

Sources & evidence

ORD record
ord-a6da5453ae444d699581da59b44c39f4
Source dataset
uspto-grants-1994_12
Patent number
US05371063

Reaction notes

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