2,4,6-Trimethylpyridine → 2-[4-chloro-(Z)-2-buten-1-yloxy]acetic Acid Tert-Butyl Ester

HRID 1271256Notes

Reaction equation

HRID 1271256 reaction equation
[C:1]([O:5][C:6](=[O:14])[CH2:7][O:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12]O)([CH3:4])([CH3:3])[CH3:2].N1C(C)=CC(C)=CC=1C.[Cl-].[Li+].CS([Cl:30])(=O)=O>CN(C)C=O>[C:1]([O:5][C:6](=[O:14])[CH2:7][O:8][CH2:9]/[CH:10]=[CH:11]\[CH2:12][Cl:30])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 865924602-[4-hydroxy-(Z)-2-buten-1-yloxy]acetic Acid Tert-Butyl Ester

Product 1

HCID 865924612-[4-chloro-(Z)-2-buten-1-yloxy]acetic Acid Tert-Butyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 420 mg of 2-[4-hydroxy-(Z)-2-buten-1-yloxy]acetic acid tert-butyl ester in 10 ml of N,N-dimethylformamide, 1.00 g of 2,4,6-collidine and 350 mg of lithium chloride were added. While stirring under ice cooling, 0.64 ml of methanesulfonyl chloride was added dropwise, followed by stirring at room temperature for 2 hours. The reaction solution was extracted with ethyl acetate after adding iced water, and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain 350 mg of the desired compound as a colorless oily substance.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. additionafter adding iced water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7c3322c9726b4171a192f7c733e76aa9
Source dataset
uspto-grants-2007_04
Patent number
US07205302B2

Reaction notes

Loading…