Ethanol → HCID 18433851, compound

HRID 2305943Notes

Reaction equation

HRID 2305943 reaction equation
C(N1C=CN=C1)(N1[CH:7]=[CH:6]N=C1)=O.[CH:13]1([CH:18]([CH3:24])[CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH2:17][CH2:16][CH2:15][CH2:14]1.CC[O-].[Na+].C(O)C>C1COCC1.[Na]>[CH:13]1([CH:18]([CH3:24])[CH2:19][CH2:20][C:21]([O:23][CH2:6][CH3:7])=[O:22])[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

7

Reactant 4

HCID 702EthanolHCID 682631,1'-CarbonyldiimidazoleHCID 2288754-cyclopentylpentanoic acidHCID 2723922Sodium ethoxide

Product 1

HCID 18433851HCID 18433851, compoundYield 48,313.398%

Reagents, catalysts & solvents 2

HCID 5360545SodiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1,1′-Carbonyldiimidazole (101 g; 0.62 mmol) was added portionwise to 4-cyclopentylpentanoic acid (100 g; 0.58 mol) in THF (500 ml). After the gas evolution ceased, the reaction mixture was reacted with sodium ethylate solution prepared from sodium (0.3 g; 13 mmol) and ethanol (500 ml), stirred at room temperature for 2.5 hours, and the solvent evaporated in vacuo. The residue was dissolved in ether (300 ml), washed successively with water (300 ml), 1 N NaOH (300 ml), and 1 N HCl (300 ml), dried (MgSO4), concentrated in vacuo, and distilled over a 10 cm Vigreux column (66° C./0.08 torr) to give 59.4 g (52% yield) of ethyl 4-cyclopentylpentanoate.

Workup

  1. customthe solvent evaporated in vacuo
  2. dissolutionThe residue was dissolved in ether (300 ml)
  3. washwashed successively with water (300 ml), 1 N NaOH (300 ml), and 1 N HCl (300 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. distillationdistilled over a 10 cm Vigreux column (66° C./0.08 torr)

Sources & evidence

ORD record
ord-14bea1b2529741d0977b86e863589352
Source dataset
uspto-grants-2002_08
Patent number
US06441052B1

Reaction notes

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