Iodoethane → HCID 54194196, compound

HRID 343285Notes

Reaction equation

HRID 343285 reaction equation
[Cl:1][C:2]1[C:3]([C:12]2[CH:32]=[CH:31][C:15]([O:16][CH2:17][C:18]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:19]=3[O:20][CH:21]([CH3:25])[C:22]([OH:24])=[O:23])=[CH:14][CH:13]=2)=[N:4][N:5]([CH3:11])[C:6]=1[O:7][CH:8]([F:10])[F:9].[CH2:33](I)[CH3:34]>C(#N)C>[Cl:1][C:2]1[C:3]([C:12]2[CH:13]=[CH:14][C:15]([O:16][CH2:17][C:18]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:19]=3[O:20][CH:21]([CH3:25])[C:22]([O:24][CH2:33][CH3:34])=[O:23])=[CH:31][CH:32]=2)=[N:4][N:5]([CH3:11])[C:6]=1[O:7][CH:8]([F:9])[F:10]

Participants

4

Reactant 2

HCID 6340IodoethaneHCID 54361466HCID 54361466, compound

Product 1

HCID 54194196HCID 54194196, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A stirred solution of 1.6 grams (0.003 mole) of 2-[2-[4-(4-chloro-5-difluoromethoxy-1-methylpyrazol-3-yl)phenoxymethyl]-5-methylphenoxy]-propanoic acid, 0.32 mL (0.004 mole) of ethyl iodide, and 0.49 mL (0.3 mole) of 1,8-diazobicyclo[5.4.0]undec-7-ene (DBU) in 40 mL of acetonitrile was heated at reflux for two hours. The reaction mixture was then cooled and concentrated under reduced pressure to a residue. The residue was taken up in water and extracted with three 60 mL portions of ethyl acetate. The combined extracts were dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel, using 3:7 diethyl ether in heptane as the eluant. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.9 gram of title compound. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureat reflux for two hours
  2. temperatureThe reaction mixture was then cooled
  3. concentrationconcentrated under reduced pressure to a residue
  4. extractionextracted with three 60 mL portions of ethyl acetate
  5. dry with materialThe combined extracts were dried with magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure to a residue
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0a71ab43a93d482f87f3e631ac93ba68
Source dataset
uspto-grants-1999_01
Patent number
US05861359

Reaction notes

Loading…