Sodium Iodide → 2-(2-Pyrrolidin-1-yl-ethoxy)-benzaldehyde

HRID 85122Notes

Reaction equation

HRID 85122 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5]1[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=1[CH:7]=[O:8].[NH:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1.C([O-])([O-])=O.[K+].[K+].[Na+].[I-]>CN(C=O)C.O>[N:13]1([CH2:2][CH2:3][O:4][C:5]2[CH:12]=[CH:11][CH:10]=[CH:9][C:6]=2[CH:7]=[O:8])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 38414102-(2-Chloroethoxy)benzaldehyde

Product 1

HCID 65042272-(2-Pyrrolidin-1-yl-ethoxy)-benzaldehydeYield 55%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(2-chloroethoxy)benzaldehyde (40; 2.5 g, 13.5 mmol), pyrrolidine (172; 1.9 g, 26.8 mmol), K2CO3 (3.8 g, 27.2 mmol) and NaI (0.6 g, 4.2 mmol) in DMF (50 mL) was stirred at 80° C. for 12 h. Water (200 mL) was added and the mixture was extracted with ethyl acetate (3×150 mL). The combined organic layers were washed brine (3×50 mL), dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by chromatography (dichloromethane:methanol=100:1) to give 2-(2-(pyrrolidin-1-yl)ethoxy)benzaldehyde 41 (1.63 g, 7.43 mmol, 55%) as a pale yellow solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×150 mL)
  2. washThe combined organic layers were washed brine (3×50 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography (dichloromethane:methanol=100:1)

Sources & evidence

ORD record
ord-ab63f02833d04c00b48e46ae41dd66a2
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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