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

HRID 342680Notes

Reaction equation

HRID 342680 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-9b2ac6b5ed9c4e76ab3c9f4a42d795b6
Source dataset
uspto-grants-1999_01
Patent number
US05859029

Reaction notes

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