Dimethyl Sulfate → HCID 53976856, compound

HRID 1680509Notes

Reaction equation

HRID 1680509 reaction equation
[N+:1]([CH:4]([CH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9](=[O:16])[O:8]1)[CH2:5][CH3:6])([O-:3])=[O:2].[C:17](=O)([O-])[O-].[K+].[K+].S(OC)(OC)(=O)=O>CC(C)=O>[CH3:17][O:8][C:9](=[O:16])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=1[CH:7]=[C:4]([N+:1]([O-:3])=[O:2])[CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 12901823HCID 12901823, compound

Product 1

HCID 53976856HCID 53976856, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 1,3-dihydro-3-(1-nitropropyl)-isobenzofuran-1-one (53 g, described in Example 27), potassium carbonate (64 g) and dimethyl sulfate (45.4 g) in acetone (1.5 l) is stirred at room temperature for 18 hr and filtered. The filtrate is evaporated and the residue is chromatographed on silica gel using hexane-diethyl ether (4:1). The eluates are evaporated to give the title compound (49 g), nmr (CDCl3) δ1.15(t), 2.65(q), 3.94(s), 7.55(m), 8.2(m) and 8.45(s).

Workup

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

Sources & evidence

ORD record
ord-d5018d0b5185430592edd857889a0018
Source dataset
uspto-grants-1981_06
Patent number
US04273773

Reaction notes

Loading…