Iodoethane → HCID 18366004, compound

HRID 380740Notes

Reaction equation

HRID 380740 reaction equation
[OH:1][CH:2]1[CH2:6][O:5][CH2:4][CH:3]1[O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:11]#[N:12].[H-].[Na+].[CH2:20](I)[CH3:21]>CN(C)C=O>[CH2:20]([O:1][CH:2]1[CH2:6][O:5][CH2:4][CH:3]1[O:7][C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[O:16][CH3:17])[C:11]#[N:12])[CH3:21]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 18366005HCID 18366005, compound

Product 1

HCID 18366004HCID 18366004, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
40 °C

Procedure

1.0 g (4.2 mmol) of 3-(4-hydroxytetrahydrofuran-3-yloxy)-4-methoxybenzonitrile (A15) in 5 ml of dimethylformamide are added dropwise under a nitrogen atmosphere to a solution of 140 mg (4.6 mmol) of sodium hydride in 5 ml of dimethylformamide and the mixture is heated at 40° C. for 1 h. 600 μl (7.5 mmol) of ethyl iodide, dissolved in 1 ml of dimethylformamide, are then added dropwise at RT. The mixture is stirred at RT for 2 h, concentrated, treated with 25 ml of water and acidified with 2 N hydrochloric acid. After extraction with 3×25 ml of ethyl acetate, the combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate and concentrated. For further purification, the product is chromatographed on silica gel [toluene/ethyl acetate=4:1]. The product-containing fractions are concentrated and the residue is crystallized from isopropanol. 660 mg of the title compound of m.p. 64-66° C. are obtained.

Workup

  1. additionare then added dropwise at RT
  2. concentrationconcentrated
  3. additiontreated with 25 ml of water
  4. extractionAfter extraction with 3×25 ml of ethyl acetate
  5. washthe combined organic phases are washed with saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customFor further purification
  9. customthe product is chromatographed on silica gel [toluene/ethyl acetate=4:1]
  10. concentrationThe product-containing fractions are concentrated
  11. customthe residue is crystallized from isopropanol

Sources & evidence

ORD record
ord-6f4692d2cbe74a3f9edf7af6529eb4c6
Source dataset
uspto-grants-2001_10
Patent number
US06303789B1

Reaction notes

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