Chlorotrimethylsilane → HCID 53854776, compound

HRID 231097Notes

Reaction equation

HRID 231097 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][CH:11]=[O:12])[CH:6]=[CH:7][CH:8]=1)#[N:2].[CH3:13][Si:14](Cl)([CH3:16])[CH3:15].C(N(CC)CC)C>CN(C)C=O>[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][CH:10]=[CH:11][O:12][Si:14]([CH3:16])([CH3:15])[CH3:13])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 138542633-(3-Oxopropyl)benzonitrile

Product 1

HCID 53854776HCID 53854776, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A stirred solution of 3-(3-cyanophenyl)propanal (3.1 g), trimethylsilyl chloride (3.0 ml) and triethylamine (6.5 ml) in dimethylformamide (45 ml) was heated under reflux on an oil bath at 150°-160° C. for 4 hours. The mixture was cooled and filtered and the filtrate was diluted with hexane (200 ml) and rapidly washed successively with cold sodium bicarbonate solution, cold dilute hydrochloric acid and cold sodium bicarbonate solution again. The hexane solution was dried and evaporated and the residue was distilled under vacuum in a bulb-to-bulb apparatus to give the product as a colourless oil, b.p. 140°-150° C./0.1 mm.

Workup

  1. temperatureunder reflux on an oil bath at 150°-160° C. for 4 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. additionthe filtrate was diluted with hexane (200 ml)
  5. washrapidly washed successively with cold sodium bicarbonate solution, cold dilute hydrochloric acid and cold sodium bicarbonate solution again
  6. dry with materialThe hexane solution was dried
  7. customevaporated
  8. distillationthe residue was distilled under vacuum in a bulb-to-bulb apparatus

Sources & evidence

ORD record
ord-e68638083daa49b1aef8e24ca09ec15b
Source dataset
uspto-grants-1989_07
Patent number
US04845110

Reaction notes

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