tert-Butanol → HCID 69053669, compound

HRID 1727196Notes

Reaction equation

HRID 1727196 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([CH3:10])[C:8]#[N:9].C(O)(C)(C)C.[C:16]([O:20][CH3:21])(=[O:19])[CH:17]=[CH2:18]>O>[C:8]([C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)([CH3:10])[CH2:18][CH2:17][C:16]([O:20][CH3:21])=[O:19])#[N:9]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 7294Methyl AcrylateHCID 12272524HCID 12272524, compound

Product 1

HCID 69053669HCID 69053669, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a dried flask under nitrogen was added 2-(2-pyridinyl)-propanenitrile (Preparation 43, 6.26 g, 47.4 mmol), t-butanol (30 ml), Triton B (6.66 g, 39.8 mmol) and methyl acrylate (6.12 g, 71.1 mmol). The reaction mixture was heated at reflux for 2.5 h. The solid was removed, and the filtrate concentrated in vacuo to give a yellow oil. Water (30 ml) was added and the product was extracted with diethyl ether. The organic extracts were dried (Na2SO4) and concentrated in vacuo to give a light yellow oil (4.32 g, 42%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2.5 h
  3. customThe solid was removed
  4. concentrationthe filtrate concentrated in vacuo
  5. customto give a yellow oil
  6. extractionthe product was extracted with diethyl ether
  7. dry with materialThe organic extracts were dried (Na2SO4)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-77fbd955da8d44b881832824574f1702
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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