3-Cyclopentylpropionyl chloride → HCID 57435105, compound

HRID 1366929Notes

Reaction equation

HRID 1366929 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[CH:9][CH:10]=1)=[O:5])[CH3:2].[Cl-].[Al+3].[Cl-].[Cl-].[CH:15]1([CH2:20][CH2:21][C:22](Cl)=[O:23])[CH2:19][CH2:18][CH2:17][CH2:16]1>ClC(Cl)C>[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([C:22](=[O:23])[CH2:21][CH2:20][CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 660393-Cyclopentylpropionyl chlorideHCID 255670Ethyl 1H-pyrrole-2-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 57435105HCID 57435105, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

Ethylpyrrole-2-carboxylate (1.8593 g, 13.36 mmol) in a minimal amount of dichloroethane was added to an ice cooled stirring mixture of aluminum chloride (3.5756 g, 26.82 mmol) and 3-cyclopentylpropionyl chloride (4.1 mL, 26.59 mmol) in dichloroethane (20 mL, 0.66 M) under N2. The ice bath was removed, and the reaction was stirred at room temperature for 4 h. 18.18 g (2.6 mMol/g) Polyamine resin HL (200-400 mesh) and dichloroethane (20 mL) were added, and the reaction was stirred for ˜60 min. The reaction was then filtered through a glass-fritted funnel directly into ice water. The resin was rinsed with CH2Cl2, then the organic layers were removed, dried with Na2SO4, filtered and concentrated. The crude product was recrystallized from Hexanes/Ethyl acetate. The crude was dissolved in a minimal amount of hot EtOAc, then allowed to slowly cool to room temperature. When no product crystallized, a small amount of hexanes was pipetted down the sides of the flask. Pure crystals of desired product (2.3068 g, 65.6%) were obtained after sitting overnight. 1H (CDCl3, 400 MHz): δ 10.04 (1H, broad s), 7.55 (1H, s), 7.29 (1H, s), 4.34 (2H, q, J=7.1 Hz), 2.77 (2H, t, J=7.6 Hz), 1.85-1.67 (5H, m), 1.64-1.46 (4H, m), 1.36 (3H, t, J=7.1 Hz), 1.78-1.06 (2H, m) ppm. 13C (CDCl3, 100 MHz): δ 196.38, 161.09, 127.03, 126.14, 124.05, 114.76, 60.91, 39.82, 39.06, 32.53, 30.82, 25.11, 14.31 ppm. DEPT (CDCl3, 100 MHz): CH3 carbons: 14.31; CH2 carbons: 60.91, 39.06, 32.53, 30.82, 25.11; CH carbons: 126.14, 114.76, 39.82 ppm. HPLC: 10.800 min.

Workup

  1. temperaturecooled
  2. customThe ice bath was removed
  3. stirringthe reaction was stirred at room temperature for 4 h
  4. addition18.18 g (2.6 mMol/g) Polyamine resin HL (200-400 mesh) and dichloroethane (20 mL) were added
  5. stirringthe reaction was stirred for ˜60 min
  6. filtrationThe reaction was then filtered through a glass-fritted funnel directly into ice water
  7. washThe resin was rinsed with CH2Cl2
  8. customthe organic layers were removed
  9. dry with materialdried with Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe crude product was recrystallized from Hexanes/Ethyl acetate
  13. dissolutionThe crude was dissolved in a minimal amount of hot EtOAc
  14. customWhen no product crystallized

Sources & evidence

ORD record
ord-cd233bcfe1f54c36b9212260fc44d8f5
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

Loading…