Sodium Iodide → HCID 22061464, compound

HRID 1829079Notes

Reaction equation

HRID 1829079 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:7](=[O:8])[O:6][CH2:5]2.Cl.Cl[CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(O)C>[N:16]1([CH2:15][CH2:14][O:1][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[C:7](=[O:8])[O:6][CH2:5]3)[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 2318865-HYDROXYPHTHALIDE

Product 1

HCID 22061464HCID 22061464, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-hydroxyphthalide (1.0 g, 6.66 mmol), 4-(2-chloroethyl)-morpholine hydrochloride (1.49 g, 8.01 mmol), potassium carbonate (2.3 g, 16.6 mmol) and sodium iodide (1.0 g, 6.67 mmol) in ethanol (40 ml) was stirred at reflux under nitrogen for 18 hours. The mixture was cooled to room temperature, and filtered through celite. The filtrate solution was evaporated to dryness. The residue was partitioned between EtOAc (75 ml) and 2M HCl solution (50 ml). The organic layer was extracted with 2M HCl (2×30 ml). The aqueous layers were combined, basified with NaOH aqueous solution, and extracted with CHCl3 (3×50 ml). The organic layers were combined, dried over anhydrous Na2SO4, and evaporated to a light brown solid, which was triturated with CHCl3/Hexanes to give 5-(2-morpholin-4-yl-ethoxy)-3H-isobenzofuran-1-one as white crystals (1.43 g, 82%).

Workup

  1. temperatureat reflux under nitrogen for 18 hours
  2. filtrationfiltered through celite
  3. customThe filtrate solution was evaporated to dryness
  4. customThe residue was partitioned between EtOAc (75 ml) and 2M HCl solution (50 ml)
  5. extractionThe organic layer was extracted with 2M HCl (2×30 ml)
  6. extractionextracted with CHCl3 (3×50 ml)
  7. dry with materialdried over anhydrous Na2SO4
  8. customevaporated to a light brown solid, which
  9. customwas triturated with CHCl3/Hexanes

Sources & evidence

ORD record
ord-de749044d89e46b4ae1bd891cc070134
Source dataset
uspto-grants-2006_06
Patent number
US07060844B2

Reaction notes

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