Ethanol → HCID 18433851, compound

HRID 2185154Notes

Reaction equation

HRID 2185154 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-d18cde03a49f4d78adfc7399836d35aa
Source dataset
uspto-grants-2002_06
Patent number
US06399811B1

Reaction notes

Loading…