1,2-Dimethoxyethane → HCID 66712110, compound

HRID 1262317Notes

Reaction equation

HRID 1262317 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][CH2:5][C:6]([C:24]#[N:25])([C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([O:22][CH3:23])[CH:14]=1)[CH2:7][CH2:8][C:9](OC)=[O:10].COCCOC.[H-].[Na+]>O>[CH3:1][O:2][C:3]([CH:4]1[CH2:5][C:6]([C:24]#[N:25])([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[C:15]([O:22][CH3:23])[CH:14]=2)[CH2:7][CH2:8][C:9]1=[O:10])=[O:26]

Participants

5

Reactant 3

HCID 80711,2-DimethoxyethaneHCID 24758Sodium hydrideHCID 66712729HCID 66712729, compound

Product 1

HCID 66712110HCID 66712110, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 1-Neck round-bottom flask, 4-Cyano-4-(3-methoxy-4-nitro-phenyl)-heptanedioic acid dimethyl ester (4.20 g, 11.5 mmol), 1,2-Dimethoxyethane (80 mL, 800 mmol), and Sodium Hydride (60% dispersion mineral oil)(6:4, Sodium hydride:Mineral Oil, 1.38 g, 34.6 mmol) were added, and heated to reflux overnight. The reaction was cooled to room temperature. Water was added to quenched the excess NaH. 2N HCl was added to adjust pH to 2. The reaction was partitioned with water and DCM. The organic was separated, washed with Brine and dried over Na2SO4. The solid was filtered and washed with DCM. The solvent was removed under vacuum. The reaction mixture was purified via ISCO column chromatography with hexane and EtOAc. The collected fractions afforded 5-Cyano-5-(3-methoxy-4-nitro-phenyl)-2-oxo-cyclohexanecarboxylic acid methyl ester as an off white solid (2.00, 59%).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. customto quenched the excess NaH
  4. addition2N HCl was added
  5. customThe reaction was partitioned with water and DCM
  6. customThe organic was separated
  7. washwashed with Brine
  8. dry with materialdried over Na2SO4
  9. filtrationThe solid was filtered
  10. washwashed with DCM
  11. customThe solvent was removed under vacuum
  12. customThe reaction mixture was purified via ISCO column chromatography with hexane and EtOAc

Sources & evidence

ORD record
ord-591efe2f45394803ad2745b8d7b5adef
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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