Ethyl phenylacetate → HCID 11074826, compound

HRID 1667173Notes

Reaction equation

HRID 1667173 reaction equation
[C:1]1([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13](#[N:16])[CH:14]=[CH2:15]>C1C=CC=CC=1.CO>[C:13]([CH2:14][CH2:15][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]([O:10][CH2:11][CH3:12])=[O:9])#[N:16]

Participants

5

Reactant 2

HCID 7590Ethyl phenylacetateHCID 7855Acrylonitrile

Product 1

HCID 11074826HCID 11074826, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-phenylacetate (5.00 g, 30.5 mmol) in benzene (50 mL) was added Triton-B (40% solution in methanol) (0.240 mL, 0.609 mmol) at 0° C. After stirring for 10 minutes, acrylonitrile (2.005 mL, 30.5 mmol) was added, and the reaction was allowed to warm to room temperature. The reaction was stirred for 3 hours, concentrated, loaded directly onto silica gel (GraceResolv High Resolution Flash Cartridge, 80 g) and eluted using a gradient of 5% to 40% ethyl acetate/hexanes over 40 minutes (flow rate=40 mL/minute). Concentration of product containing fractions provided the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.44-7.19 (m, 5H), 4.26-4.00 (m, 2H), 3.81-3.59 (m, 1H), 2.50-2.01 (m, 4H), 1.20 (t, J=7.1, 3H).

Workup

  1. stirringThe reaction was stirred for 3 hours
  2. concentrationconcentrated
  3. washeluted
  4. customover 40 minutes
  5. additionConcentration of product containing fractions

Sources & evidence

ORD record
ord-1ac0c31b6cd64fd3b9796477e023e66b
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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