Water → HCID 58092732, compound

HRID 1807698Notes

Reaction equation

HRID 1807698 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3](OS(C)(=O)=O)([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][O:13][CH3:14])=[CH:7][N:6]=1)[CH3:4].[CH3:22][Al](C)C.O>ClCCl>[CH3:14][O:13][CH2:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]([CH3:22])([CH3:4])[C:2]([F:21])([F:20])[F:1])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 16682925TrimethylaluminumHCID 58092712HCID 58092712, compound

Product 1

HCID 58092732HCID 58092732, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.7 g (4.13 mmol) methanesulfonic acid 2,2,2-trifluoro-1-(5-methoxymethoxy-pyridin-2-yl)-1-methyl-ethyl ester was dissolved in 20 ml dichloromethane. The reaction mixture was cooled to 0° C. where 2.065 ml (4.13 mmol) trimethylaluminum was added slowly. The reaction mixture was stirred at room temperature for 20 h. After that water was added slowly and the mixture was extracted 2 times with EtOAc. The combined organic layers were washed with water and brine, dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by chromatography on silicagel (EtOAc, heptane) to yield to afford 0.55 g of the pure title compound. LCMS (method L): tR=1.09 min, M+H=250.

Workup

  1. additionwas added slowly
  2. extractionthe mixture was extracted 2 times with EtOAc
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by chromatography on silicagel (EtOAc, heptane)
  8. customto yield

Sources & evidence

ORD record
ord-13de605e86544188b59aab966665992b
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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