Water → N[(dimethyl-4-fluorobenzylsilyl)methyl]phthalimide

HRID 260638Notes

Reaction equation

HRID 260638 reaction equation
Cl[CH2:2][Si:3]([CH3:13])([CH3:12])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1.[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K].O>CN(C)C=O>[CH3:12][Si:3]([CH2:2][N:18]1[C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]2[C:14]1=[O:24])([CH3:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 15338764Chloromethyl-dimethyl(4-fluorobenzyl)silaneHCID 24194345Phthalimide potassium salt

Product 1

HCID 15225545N[(dimethyl-4-fluorobenzylsilyl)methyl]phthalimideYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Chloromethyl-dimethyl-4-fluorobenzylsilane (2.01 g, 9.33 mmol) and potassium phthalimide (1.90 g), 10.27 mmol) were heated in dry dimethylformamide (30 ml) at 70° C. for 5 hours and then the mixture was poured into water and extracted with ether. The ether solution was washed with water, brine, dried and evaporated. Chromatography (silica gel, ether/hexane-20/80) afforded N[(dimethyl-4-fluorobenzylsilyl)methyl]phthalimide as a white powder (2.90 g, 95% yield) 1H NMR (CDCl3, TMS) δ: 0.20 (s,6H), 2.25 (s,2H), 3.27 (s,2H), 6.83-7.13 (m,4H), 7.67-7.97 (m,4H).

Workup

  1. extractionextracted with ether
  2. washThe ether solution was washed with water, brine
  3. customdried
  4. customevaporated

Sources & evidence

ORD record
ord-2029036e7e2747aab80b073b32677ebe
Source dataset
uspto-grants-1996_06
Patent number
US05529988

Reaction notes

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