Chlorodimethylsilane → HCID 57147164, compound

HRID 1770325Notes

Reaction equation

HRID 1770325 reaction equation
[Cl:1][SiH:2]([CH3:4])[CH3:3].[C:5]([CH2:7][C:8]([O:10][CH2:11][C:12]#[CH:13])=[O:9])#[N:6]>C1(C)C=CC=CC=1.[Pt]>[C:5]([CH2:7][C:8]([O:10][CH2:11][CH:12]=[CH:13][Si:2]([Cl:1])([CH3:4])[CH3:3])=[O:9])#[N:6]

Participants

5

Reactant 2

HCID 66108ChlorodimethylsilaneHCID 14972819Prop-2-yn-1-yl cyanoacetate

Product 1

HCID 57147164HCID 57147164, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Chlorodimethylsilane (29.59 g, 0.313 mol) was added dropwise at 80° C. to a solution of 35.0 g (0.284 mol) propargyl cyanoacetate, 0.1 g of a solution of 1,3 divinyl- 1,1,3,3-tetramethyldisiloxane/Pt(0) complex containing 5 wt % platinum in xylenes (Karstedt catalyst) and 50 ml toluene under a nitrogen blanket. The reaction was stirred 3 hours at 80° C. after the addition. An IR spectrum confirmed disappearance of Sill at 2160 cm-1. After removing low-boiling volatiles by rotary evaporation, the crude product was purified by vacuum distillation. Upon removal of a small forecut at 80° C. at 0.1 mm Hg, the product distilled at 100°-115° C. at 0.1 m Hg. Yield: 47.1 g (76%) of a clear, greenish tinged liquid. Its structure was confirmed to be cyanoacetoxypropenylchlorodimethylsilane by IR and proton NMR.

Workup

  1. additionafter the addition
  2. customAfter removing low-boiling volatiles
  3. customby rotary evaporation
  4. distillationthe crude product was purified by vacuum distillation
  5. customUpon removal of a small forecut at 80° C. at 0.1 mm Hg
  6. distillationthe product distilled at 100°-115° C. at 0.1 m Hg

Sources & evidence

ORD record
ord-49a326816674434bb3c354e21e978a88
Source dataset
uspto-grants-1995_01
Patent number
US05386047

Reaction notes

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