18-Crown-6 → HCID 57687132, compound

HRID 1509971Notes

Reaction equation

HRID 1509971 reaction equation
CO[C:3]1C(O)=C[C:6]([O:10][CH3:11])=[CH:5][C:4]=1[N+:12]([O-:14])=[O:13].[CH2:15]1[O:32][CH2:31][CH2:30][O:29][CH2:28][CH2:27][O:26][CH2:25][CH2:24][O:23]CCOCCOC1.BrCC1OCCO1.C([O-])(O)=O.[Na+]>CCOCC.CN(C=O)C>[CH3:11][O:10][C:6]1[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=[C:31]([O:32][CH3:15])[C:30]=1[O:29][CH2:28][CH:27]1[O:23][CH2:24][CH2:25][O:26]1

Participants

7

Reactant 4

HCID 2855718-Crown-6HCID 780681,3-Dioxolane, 2-(bromomethyl)-HCID 516892Sodium BicarbonateHCID 68900277HCID 68900277, compound

Product 1

HCID 57687132HCID 57687132, compoundYield 60.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a mixture of 2,5-dimethoxy-3-hydroxynitrobenzene (2.0 g, 8.43 mmol), 18-crown-6 (2.97 g, 8.43 mmol) and bromomethyl dioxolane (4.22 g, 25.3 mmol) was added DMF (60 ml). The solution was then heated for a total of 1.5 h in the CEM microwave at 140° C., initial voltage=300 W. The solution was poured on to a mixture of sat. NaHCO3 and Et2O, the layers separated and the aqueous extracted with Et2O. The combined organic layers were washed with water (4×50 ml), 1M HCl (50 ml) and brine (2×50 ml), dried over MgSO4 filtered and evaporated. Hexanes were added to the solid residue and the resulting suspension stirred for 1 h. The product was isolated by filtration and dried in a vacuum oven to afford the title compound (1.45 g, 57%). m/z 286 [M+H]+.

Workup

  1. customthe layers separated
  2. extractionthe aqueous extracted with Et2O
  3. washThe combined organic layers were washed with water (4×50 ml), 1M HCl (50 ml) and brine (2×50 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. additionHexanes were added to the solid residue
  8. customThe product was isolated by filtration
  9. customdried in a vacuum oven

Sources & evidence

ORD record
ord-1e1ab3d511424449bbfcae1a5284991b
Source dataset
uspto-grants-2012_07
Patent number
US08211900B2

Reaction notes

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