Dimethyl Sulfate → HCID 53939584, compound

HRID 1680508Notes

Reaction equation

HRID 1680508 reaction equation
[N+:1]([CH:4]([CH:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](=[O:15])[O:7]1)[CH3:5])([O-:3])=[O:2].S(OC)(O[CH3:20])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH3:20][O:7][C:8](=[O:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=1[CH:6]=[C:4]([N+:1]([O-:3])=[O:2])[CH3:5]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 27634793-(1-Nitroethyl)-2-benzofuran-1(3H)-one

Product 1

HCID 53939584HCID 53939584, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 1,3-dihydro-3-(1-nitroethyl)-isobenzofuran-1-one [2.0 g, described by J. J. Stehle et al., J. Org. Chem., 10, 429 (1945)], dimethyl sulfate (1.6 ml) and potassium carbonate (2.4 g) in acetone (50 ml) is stirred at 25° C. for 18 hr under dry conditions. The mixture is filtered and the filtrate is evaporated. The residue is chromatographed on silica gel using benzene and the eluates are evaporated to give the title compound (1.672 g), nmr (CDCl3) δ2.25(s), 3.91(s), 7.40(s), 7.60(m), 8.18(s) and 8.50(s).

Workup

  1. filtrationThe mixture is filtered
  2. customthe filtrate is evaporated
  3. customThe residue is chromatographed on silica gel
  4. customthe eluates are evaporated

Sources & evidence

ORD record
ord-88dcd485b7454b8bb0da29b8c1df1343
Source dataset
uspto-grants-1981_06
Patent number
US04273773

Reaction notes

Loading…