Cesium carbonate → Phthalimide

HRID 74393Notes

Reaction equation

HRID 74393 reaction equation
OC1C=C(C=CC=1)OCC[N:8]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18].C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1>[C:16]1(=[O:17])[NH:8][C:9](=[O:18])[C:10]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:15]12

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 580275342-[2-(3-Hydroxy-phenoxy)-ethyl]-isoindole-1,3-dione

Product 1

HCID 6809Phthalimide

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-[2-(3-hydroxy-phenoxy)-ethyl]-isoindole-1,3-dione (24) (5 g, 17.6 mmol), 4-bromoethyl butyrate (3.0 mL, 21.28 mmol) and cesium carbonate (6.2 g, 35.38 mmol) in NMP (30 mL) was warmed at 70° C. for 12 h. The mixture was cooled to room temperature and poured into crushed ice. This mixture was extracted with EtOAc and the organic layer was washed with water, then brine, dried over Na2SO4 and concentrated under reduced pressure. Purification by flash chromatography (0 to 10% EtOAc-hexanes gradient) gave ether 5 as clear oil. Yield (3.33 g, 47%): 1H NMR (400 MHz, CDCl3) δ 7.85-7.87 (m, 2H), 7.71-7.74 (m, 2H), 7.10-7.14 (m, 1H), 6.42-6.47 (m, 3H), 4.08-4.22 (m, 6H), 3.95 (t, J=6.0 Hz, 2H), 2.49 (t, J=7.4 Hz, 2H), 2.04-2.11 (m, 2H), 1.26 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. additionpoured
  3. custominto crushed ice
  4. extractionThis mixture was extracted with EtOAc
  5. washthe organic layer was washed with water
  6. dry with materialbrine, dried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customPurification by flash chromatography (0 to 10% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-859f4ae9b45e49698bb8f0454559581d
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Reaction notes

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