Ethanol → 4-(2-Tetrahydropyranyloxyethyl)-4-(3,4-dichlorophenyl)-2-pyrrolidone

HRID 2257059Notes

Reaction equation

HRID 2257059 reaction equation
[C:1]([C:3]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([Cl:26])[CH:20]=1)([CH2:10][CH2:11][O:12][CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1)[CH2:4][C:5](OCC)=[O:6])#[N:2].CCO.C([O-])(O)=O.[Na+]>O>[Cl:26][C:21]1[CH:20]=[C:19]([C:3]2([CH2:10][CH2:11][O:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[CH2:1][NH:2][C:5](=[O:6])[CH2:4]2)[CH:24]=[CH:23][C:22]=1[Cl:25]

Participants

5

Reactant 3

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 21197693Ethyl 3-cyano-3-(3,4-dichlorophenyl)-5-(tetrahydropyran-2-yloxy)pentanoate

Product 1

HCID 211976714-(2-Tetrahydropyranyloxyethyl)-4-(3,4-dichlorophenyl)-2-pyrrolidoneYield 83.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 8 g of the compound obtained in step B in 100 ml of 100° EtOH, 5 ml of water and 0.6 g of NaHCO3 is hydrogenated at atmospheric pressure and at RT. The catalyst is filtered off and the filtrate is evaporated under vacuum. The residue is extracted with DCM, the extract is washed with water and dried over MgSO4 and the solvent is evaporated off under vacuum to give 6 g of the expected product.

Workup

  1. customis hydrogenated at atmospheric pressure and at RT
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated under vacuum
  4. extractionThe residue is extracted with DCM
  5. washthe extract is washed with water
  6. dry with materialdried over MgSO4
  7. customthe solvent is evaporated off under vacuum

Sources & evidence

ORD record
ord-43882d66ef404f03a39c2538bf472814
Source dataset
uspto-grants-1997_08
Patent number
US05656639

Reaction notes

Loading…