Formaldehyde → 3-Trimethylsilylpropyl 2-cyanoacrylate

HRID 1708648

반응식

HRID 1708648 반응식
[C:1]([CH2:3][C:4]([O:6][CH2:7][CH2:8][CH2:9][Si:10]([CH3:13])([CH3:12])[CH3:11])=[O:5])#[N:2].C=O.N1CCCC[CH2:17]1.O>C(OC(=O)C)CCC>[C:1]([C:3](=[CH2:17])[C:4]([O:6][CH2:7][CH2:8][CH2:9][Si:10]([CH3:11])([CH3:13])[CH3:12])=[O:5])#[N:2]

참가 물질

6

반응물 4

HCID 712Formaldehyde2회HCID 962WaterHCID 8082PiperidineHCID 18959748HCID 18959748, 화합물

생성물 1

HCID 200960453-Trimethylsilylpropyl 2-cyanoacrylate

시약·촉매·용매 1

HCID 31272Butyl Acetate용매

실험 절차

3-trimethylsilylpropyl 2-cyanoacetate (31.84 g, 0.16 moles) prepared as described in Example 1, was added dropwise over 10 minutes to a stirred solution of paraformaldehyde (4.8 g, 0.16 moles formaldehyde) and piperidine (0.12 g) in n-butylacetate at 70° C. The mixture was heated under reflux in a Dean-Stark apparatus until the quantitative amount of water expected from formaldehyde condensation had been collected (2.8 g). The mixture was allowed to cool and phosphorous pentoxide (0.57 g), p-toluenesulfonic acid (1.09 g) and 1,4-hydroquinone (2.18g) were added. The solvent was removed by distillation under reduced pressure to yield a viscous, orange/yellow coloured liquid. The liquid was fractionated under reduced pressure to give crude monomer (16.80 g b.p. 150°-180° C. at 0.7-10 mbar). Vacuum distillation of the crude material onto a catalytic quantity of methanesulfonic acid and 1,4-hydroquinone (10-4 g) afforded the pure product 3-trimethylsilylpropyl 2-cyanoacrylate as a slightly yellow coloured reactive liquid (12.45 g, 37%).

후처리

  1. temperatureThe mixture was heated
  2. customhad been collected (2.8 g)
  3. temperatureto cool
  4. additionphosphorous pentoxide (0.57 g), p-toluenesulfonic acid (1.09 g) and 1,4-hydroquinone (2.18g) were added
  5. customThe solvent was removed by distillation under reduced pressure
  6. customto yield a viscous, orange/yellow coloured liquid
  7. customto give crude monomer (16.80 g b.p. 150°-180° C. at 0.7-10 mbar)
  8. distillationVacuum distillation of the crude material onto a catalytic quantity of methanesulfonic acid and 1,4-hydroquinone (10-4 g)

출처 및 근거

ORD 기록
ord-e625dfc3581b42a2a12de75198058983
출처 데이터셋
uspto-grants-1994_10
특허 번호
US05359101

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