5-bromo-1,1-dimethoxypentane → 2-(5,5-Dimethoxypentyl)-1H-isoindole-1,3(2H)-dione

HRID 1194767Notes

Reaction equation

HRID 1194767 reaction equation
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[K].[CH3:13][O:14][CH:15]([O:21][CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19]Br>CN(C)C=O>[CH3:13][O:14][CH:15]([O:21][CH3:22])[CH2:16][CH2:17][CH2:18][CH2:19][N:5]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6]

Participants

4

Reactant 2

HCID 110746845-bromo-1,1-dimethoxypentaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 132861182-(5,5-Dimethoxypentyl)-1H-isoindole-1,3(2H)-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of potassium phthalimide (0.48 g) and 5-bromopentanal dimethyl acetal (0.50 g) in dry dimethylformamide (3 ml) was stirred at 90° for 5 h and then allowed to cool. The resultant yellow suspension was then partitioned between water (30 ml) and ethyl acetate (3×30 ml). The combined organic extracts were then dried (Na2SO4) and concentrated in vauco.

Workup

  1. temperatureto cool
  2. customThe resultant yellow suspension was then partitioned between water (30 ml) and ethyl acetate (3×30 ml)
  3. dry with materialThe combined organic extracts were then dried (Na2SO4)
  4. concentrationconcentrated in vauco

Sources & evidence

ORD record
ord-7b14b9fab9fc426eb1278cc5b0f1bd6e
Source dataset
uspto-grants-1989_03
Patent number
US04816470

Reaction notes

Loading…