1-Bromopropane → HCID 178459261, compound

HRID 1363717Notes

Reaction equation

HRID 1363717 reaction equation
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH2:4][CH2:3]1.[H-].[Na+].[CH2:21](Br)[CH2:22][CH3:23]>CN(C=O)C>[CH2:21]([O:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([N:8]2[C:9](=[O:18])[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]2=[O:17])[CH2:6][CH2:7]1)[CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 178515017HCID 178515017, compound

Product 1

HCID 178459261HCID 178459261, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of trans-2-(4-hydroxycyclohexyl)-isoindole-1,3-dione (13 g, 53 mmol) in dry DMF (50 mL) was added molecular sieves (4 Å, 6 mL). The mixture was stirred for 30 min at rt. NaH (5.3 g 60% in oil, 132.5 mmol) was washed with hexanes before it was added in portions to the reaction mixture. The mixture was stirred for 30 min before propylbromide (48.1 mL, 530 mmol) was added. The reaction mixture was stirred for 16 hours before the reaction mixture was filtered. The filtrate was added water (100 mL) and extracted with Et2O (250 mL). The organic phase was washed with brine (3×50 mL) and dried (MgSO4) and the solvent was removed in vacuo. The crude product was purified by column chromatography (silica gel, heptane-EtOAc (4:1). The first band was collected to give 6.6 g (43%) of trans-2-(4-propyloxycyclohexyl)-isoindole-1,3-dione.

Workup

  1. additionwas added in portions to the reaction mixture
  2. additionwas added
  3. stirringThe reaction mixture was stirred for 16 hours before the reaction mixture
  4. filtrationwas filtered
  5. additionThe filtrate was added water (100 mL)
  6. extractionextracted with Et2O (250 mL)
  7. washThe organic phase was washed with brine (3×50 mL)
  8. dry with materialdried (MgSO4)
  9. customthe solvent was removed in vacuo
  10. customThe crude product was purified by column chromatography (silica gel, heptane-EtOAc (4:1)
  11. customThe first band was collected

Sources & evidence

ORD record
ord-68437120d5054fad855ddd62d26df350
Source dataset
uspto-grants-2011_02
Patent number
US07884210B2

Reaction notes

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