Dabco → HCID 12917176, compound

HRID 1515781Notes

Reaction equation

HRID 1515781 reaction equation
[CH2:1]([S:3][C:4](=[O:11])[CH2:5][C:6]([S:8][CH2:9][CH3:10])=[O:7])[CH3:2].N12CCN(CC1)CC2.[C:20]1(=[O:25])[CH2:24][CH2:23][CH:22]=[CH:21]1>COCCOC>[CH2:1]([S:3][C:4](=[O:11])[CH:5]([CH:22]1[CH2:23][CH2:24][C:20](=[O:25])[CH2:21]1)[C:6]([S:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

5

Reactant 3

HCID 9237DabcoHCID 135882-Cyclopenten-1-oneHCID 11074256HCID 11074256, compound

Product 1

HCID 12917176HCID 12917176, compoundYield 86.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of dithiomalonic acid di-S-ethyl ester (42.3 g, 0.22 mol) and 1,4-diazabicyclo[2,2,2]octane (24.7 g, 0.22 mol), cyclopent-2-enone (17.6 g, 0.21 mol) in 1,2-dimethoxyethane (300 mL) was stirred at room temperature under nitrogen for 48 h. The mixture was concentrated in vacuo to give a residue which was purified by flash column chromatography (QingDao silica gel, 200-300 mesh, 5% ethyl acetate/pentane) afforded 2-(3-oxo-cyclopentyl)-dithiomalonic acid di-S-ethyl ester as a white solid (50.0 g, 82%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give a residue which
  3. customwas purified by flash column chromatography (QingDao silica gel, 200-300 mesh, 5% ethyl acetate/pentane)

Sources & evidence

ORD record
ord-9393c068d452434fa192b454e423c545
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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