2,4,6-Trimethylpyridine → HCID 53823294, compound

HRID 1646229Notes

Reaction equation

HRID 1646229 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([CH:9]=[CH:10][CH2:11]O)=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16].[Cl-].[Li+].N1C(C)=CC(C)=CC=1C.CS([Cl:33])(=O)=O>CN(C)C=O.O>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:14]=[CH:13][C:8]([CH:9]=[CH:10][CH2:11][Cl:33])=[CH:7][C:6]=1[N+:15]([O-:17])=[O:16]

Participants

7

Reactant 4

HCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 54260281HCID 54260281, compound

Product 1

HCID 53823294HCID 53823294, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Under a current of argon, a solution of 1.50 g of 4-methoxymethoxy-3-nitrocinnamyl alcohol in 15 ml of dimethyl formamide and 292 mg of anhydrous lithium chloride and 0.9 ml of 2,4,6-collidine added thereto as kept cooled with ice were stirred for 10 minutes and the produced mixture and 0.5 ml of methanesulfonyl chloride added as kept cooled with ice were stirred for four hours. The resultant reaction mixture was combined with water and extracted from ethyl acetate. The consequently separated organic layer was washed with saturated saline solution and dried with anhydrous sodium sulfate. By concentrating the residue from drying under a vacuum, 1.62 g of 4-methoxymethoxy-3-nitrocinnamyl chloride was obtained in the form of a colorless oily substance. This product was put to use in its unpurified form in the following reaction.

Workup

  1. temperatureas kept cooled with ice
  2. temperatureas kept cooled with ice
  3. stirringwere stirred for four hours
  4. customThe resultant reaction mixture
  5. extractionextracted from ethyl acetate
  6. washThe consequently separated organic layer was washed with saturated saline solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. concentrationBy concentrating the residue
  9. customfrom drying under a vacuum

Sources & evidence

ORD record
ord-d743d0320870420886667367fe6a89f1
Source dataset
uspto-grants-1993_01
Patent number
US05179105

Reaction notes

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