Ammonia → Methyl 2-(2-cyanovinyl)benzoate

HRID 84929

Reaction equation

HRID 84929 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])=O.C1(P(=[CH:32][C:33]#[N:34])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N>C1(C)C=CC=CC=1>[C:33]([CH:32]=[CH:1][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])#[N:34]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 85524(Triphenylphosphoranylidene)acetonitrileHCID 243003Methyl 2-formylbenzoate

Product 1

HCID 66818837Methyl 2-(2-cyanovinyl)benzoate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Methyl 2-formylbenzoate (10 g, 60.9 mmol) was dissolved in toluene (200 mL). (Triphenylphosphoranylidene)acetonitrile (20.19 g, 67.0 mmol) was then added to the mixture. The reaction was heated at 110° C. for 20 hours, then cooled to room temperature, concentrated under vacuum and the residue was triturated with ether (2×). The ether solution was passed though a plug of silica gel to provide Example 1A (mixture of E and Z isomers). The mixture of E and Z isomers was used directly for the next step. MS (DCI+) m/z 205.0 [M+NH3]+.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under vacuum
  3. customthe residue was triturated with ether (2×)
  4. customto provide
  5. additionExample 1A (mixture of E and Z isomers)
  6. additionThe mixture of E and Z isomers

Sources & evidence

ORD record
ord-ec35e586d37f4cd1aa125441cff8df0d
Source dataset
uspto-grants-2014_09
Patent number
US08846951B2

Linked notes

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